Tag: M.W:100-200

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Pyrimidines. I. Synthesis of pyrimidinethiols》. Authors are Koppel, Henry C.; Springer, Robert Henre; Robins, Roland K.; Cheng, C. C..The article about the compound:2-Amino-6-methylpyrimidine-4-thiolcas:6307-44-4,SMILESS:SC1=CC(C)=NC(N)=N1).Computed Properties of C5H7N3S. Through the article, more information about this compound (cas:6307-44-4) is conveyed.

cf. CA 54, 6747a. The 9 previously unknown isomers of the 22 possible substituted pyrimidinethiols, containing H, HO, NH2, and SH as substituents were synthesized and methods for preparation of some of the previously reported compounds were improved. Various derivatives of RC:N.CR1:N.CR2:CH (I) were prepared for preliminary screening as antitumor agents. HOCH2CH2OH (200 ml.), 125 g. 4,5-Cl(MeS)C4H2N2, and 200 g. NaSH heated slowly to 100° with frothing and bubbling, the mixture carefully heated to 150° and kept 30 min., the solution poured into 1500 ml. H2O and the boiled, decolorized hot filtrate acidified with AcOH, the precipitate reprecipitated from hot dilute aqueous NH4OH with AcOH gave 85 g. I (R = H, R1 = R2 = SH), converted by concentrated HBr to I (R = R1 = H, R2 = SH). NaHS (42 g.) and 13 g. 4,6,2-Cl(HO)(MeS)C4HN2 in 120 ml. HOCH2CH2OH heated 30 min. at 150°, the cooled mixture poured into 500 ml. H2O and the boiled decolorized solution filtered, acidified with AcOH to pH 5 and the refiltered solution adjusted to pH 1.0 with dilute HCl, the product reprecipitated from solution in dilute NH4OH with HCl, and the product recrystallized from HCONMe2-H2O gave 9.0 g. I (R = OH, R1 = R2 = SH), m. 262-4° (method A). The appropriate chloropyrimidine (60 g.) in 500 ml. absolute alc. refluxed 3 hrs. with 150 g. NaHS, the chilled mixture filtered and the alc. washed precipitate boiled in 1 l. H2O, the decolorized solution filtered, the filtrate acidified and the precipitate recrystallized from the appropriate solvent gave RC:N.CR1: N.CR2:CR3 (II) (method B). In method C the procedure was the same but no precipitate was formed. The light yellow alc. solution was diluted with 1 l. boiling H2O and acidified and the precipitate recrystallized The appropriate chloropyrimidine (40 g.) and 40 g. (H2N)2CS in 500 ml. absolute alc refluxed 2 hrs. the mixture chilled and the precipitated ligroine-washed product purified by reprecipitation and recrystallization gave II (method D). The appropriate chloropyrimidine (35 g.) and 70 g. powd. NaHS in 400 ml. H2O was autoclaved 4 hrs. at 150°/8 atm., the solution boiled and the decolorized solution filtered, acidified with AcOH [for the preparation of I (R = NH2, R1 = SH, R2 = OH)] or dilute HCl [for the preparation of I (R = SH, R1 = R2 = OH)], and the products purified by recrystallization (method E). I (R = NH2, R1 = SH, R2 = OH) (50 g. finely powd. and dried at 100°) refluxed 2 hrs. with 150 g. P2S5 in 1.5 l. dry C5H5N, excess C5H5N evaporated in vacuo and the residue diluted cautiously with 750 ml. H2O, the mixture refluxed 2 hrs. on a steam bath with evolution of H2S, the chilled mixture filtered and adjusted to pH 2, the volume reduced to 33% in vacuo and the cooled concentrate filtered, the residue taken up in dilute NH4OH and the boiled decolorized solution filtered, acidified with dilute HCl and the precipitate recrystallized from HCONMe2-H2O gave 35 g. I (R = H2N, R1 = R2 = SH). Purified P2S5 (125 g.) and 52 g. I (R = R1 = H, R2 = OH) refluxed 1 hr. with stirring in l. C5H5N, the hot solution poured into 1 l. H2O and the solution heated on a steam bath 3 hrs., the filtered solution evaporated in vacuo to 200 ml., refrigerated and the H2O-washed product recrystallized from 500 ml. boiling H2O gave 42 g. I (R = R1 = H, R2 = SH). I(R = R2 = Cl, R1 = NH2) (33 g.) added to 1 l. 4:1 alc.-H2O containing 40 g. NaOH saturated with H2S, the mixture refluxed with stirring 2 hrs. with passage of H2S, treated with C and the filtered solution acidified with AcOH gave 42 g. I (R = SH, R1 = NH2, R2 = Cl), m. 302° (decomposition), λ 260 mμ (ε 9800, pH 1), λ 280 mμ (ε 12,500, pH 11), converted by autoclaving with NaHS to I (R = SH, R1 = R2 = OH). I (R = R2 = OH, R1 = SH)(60 g.)in 1 l. 2N NaOH stirred 3 hrs. with dropwise addition of 50 g. Me2SO4, the solution boiled with addition of C and the decolorized filtered solution acidified to pH 1.0 with HCl gave 50 g. I (R = R1 = OH, R1 = MeS) (III), m. above 360° (H2O). III (80 g.) refluxed 2 hrs. with 500 ml. POCl3, excess POCl3 removed in vacuo and the residue poured with stirring over crushed ice, the mixture stirred 20 min. at 0°, filtered and the precipitate washed in ice H2O until the pH of the washings was no longer below 5, the material dried 16 hrs. in vacuo and recrystallized from MeOH and H2O gave 64 g. I (R = R2 = Cl, R1 = MeS) (IV), m 43°. Treatment of IV with NaHS at 150° in HOCH2CH2OH gave I (R = R1 = R2 = SH). NaHS (75 g.) in 500 ml. MeOH at 50° stirred with portionwise addition of 50 g. IV, the mixture stirred 30 min. before dilution with 1 l. H2O, the solution boiled with C and the filtered solution acidified, the product reprecipitated from dilute NH4OH with AcOH, and recrystallized from HCONMe2-H2O gave 40 g. I (R = R2 = HS, R1 = MeS), m. above 360°. IV (50 g.) refluxed with stirring 4 hrs. in 500 ml. 2N NaOH, the solution decolorized and the filtered solution acidified with AcOH, the precipitate purified by reprecipitation and recrystallized from HCONMe2-H2O gave 40 g. I (R = Cl, R1 = MeS, R2 = OH), m. 208°. Absolute MeOH (150 ml.) at 0° treated with 30 g. finely powd. IV, the mixture stirred 45 min. with passage of dry Cl, filtered from 8 g. product, and the filtrate evaporated at 20° in a stream of dry air gave 12 g. product; the crops combined and recrystallized from EtOAc and C7H16 gave 17 g. I (R = R2 = Cl, R1 = MeSO2) (V), m. 119°. V (15 g.) warmed in 200 ml. N NaOH, the filtered solution chilled and the precipitate washed with cold H2O and alc., the dry salt (11.6 g.) in 150 ml. H2O carefully neutralized with HCl and the solution evaporated in vacuo, the residue taken up in boiling Me2CHOH and diluted with C7H16 gave 5 g. I (R = R2 = Cl, R1 = OH), m. 262° (Me2CHOHC7H16). The ultraviolet absorption spectra of the completed series of I showed the approx. maximum of the major peak of I in solutions at pH 1.0 were 280, 300-20, 320-40, and 360-70 mμ for 2-pyrimidinethiols, 4-pyrimidinethiols, 2,4-pyrimidinedithiols, and 4,6-pyrimidinedithiols, resp. Data for I and for a number of known thiopyrimidines, II, not previously published are recorded for comparison [R, R1, R2, R3, m.p. (solvents), and % yield given]: H, SH, H, H, 229-30° (alc.), 70; H, H, SH, H, 190-2° (H2O), 69; H, OH, SH, H, 298-300° (H2O-HCONMe2), 88; H, SH, OH, H, 310-12° (H2O), 73; H, NH2, SH, H, 231-3° (H2O-HCONMe2), 68; OH, H, SH, H, 247° (H2O), 79; H2N, H, SH, H, 306° (H2O-HCONMe2), 61; H, SH, SH, H, 300° (H2O), 70; HS, H, SH, H, 250-2° (H2O), 70; OH, SH, OH, H, above 360° (H2O-HCONMe2), 84; OH, OH, SH, H, 245° (H2O), 54; H2N, OH, SH, H, 355° (H2O-HCONMe2), 43; OH, H2N, SH, H, above 360° (H2O-HCONMe2), 82; H2N, H2N, SH, H, above 360° (reprecipitation), 50; H2N, SH, OH, H, above 360° (reprecipitation), 91; H2N, SH, H2N, H, above 360° (reprecipitation), 93; OH, SH, SH, H, 262-4° (H2O-HCONMe2), 79; H2N, SH, SH, H, above 360° (H2O-HCONMe2), 60; SH, OH, SH, H, 266-7° (H2O-HCONMe2), 46; SH, H2N, SH, H, 267° (H2O), 76; SH, SH, SH, H, above 360° (reprecipitation), 70; Cl, H2N, H, Cl, above 360° (reprecipitation), 63; Me, H2N, SH, H, 321° (reprecipitation), 84; Me, H2N, SH, Br, 207° (H2O-HCONMe2), 98; Me, SH, SH, H, above 360° (H2O-HCONMe2), 70; H, SH, SH, CO2H, 261-3° (H2O-HCONMe2), 63; SH, H, SH, Cl, 215-17° (reprecipitation), 70; SH, H, SH, Br, 213° (reprecipitation), 92; SH, H2N, SH, Ph, 266-8° (H2O-HCONMe2), 60; H, MeS, SH, H, 203° (H2O-HCONMe2), 96; Me, MeS, SH, H, 239° (H2O-HCONMe2), 78; SH, MeS, SH, H, above 360° (H2O-alc.), 80. For comparison of structure and biol. activities in pyrimidine thiols, a number of new related 4-pyrimidine thiols substituted in position 5 were synthesized. Thiopyrimidine (0.08 mole) stirred in 250 ml. N NaOH treated with a stoichiometric amount of the appropriate alkyl halide, the mixture stirred 3 hrs. and the H2O-washed precipitate recrystallized gave the corresponding alkylthiopyrimidine (method A). Similarly, the above reaction mixture on failure to give a precipitate was acidified with AcOH and the product recrystallized to yield the required alkyl thiopyrimidine (method B). The yields ranged from 80 to 95%. Phys. data for alkylthio- and aralkylthiopyrimidines are listed [R, R1, R2, R3 of formula II, method of synthesis, m.p. (solvent, if other than HCONMe2 + H2O) given]: MeS, H, OH, H, B, 230° (H2O); PhCH2S, H, OH, H, B, 238-9°; 2,4-Cl2C6H3CH2S, H, OH, H, B, 191.3°; MeS, H, H2 N, H, A, 168-70°; EtS, H, H2N, H, A, 147-9°; PhCH2S, H, H2N, H, A, 140°; 2,4-Cl2C6H3CH2S, H, H2N, H, A, 184-6°; p-O2NC6H4CH2S, H, H2N, H, A, 165-7°; MeS, H, MeS, H, A, 52-4° (C7H16); MeS, H, MeS, H2N, A, 79°; MeS, H, MeS, Cl, A, 118-20°; EtS, H, EtS, Cl, A, 58-9°; PhCH2S, H, PhCH2S, Cl, A, 86-8°; 2,4-Cl2C6H3CH2S, H 2,4-Cl2C6H3CH2S, Cl, A, 155°; MeS, H, MeS, Br, A, 155°; PrS, H, PrS, Br, A, 44-6°; PhCH2S, H, PhCH2S, Br, A, 95-7°; 2,4-Cl2C6H3CH2S, H, 2,4-Cl2C6H3CH2S, Br, A, 149°; p-O2NC6H4CH2S, H, p-O2NC6H4CH2S, Br, A, 168-70°; PhCH2S, OH, OH, H, B, 242°; H, OH, o-ClC6H4CH2S, H, A, 174-6°; H, OH, 2,4-Cl2C6H3CH2S, H, A, 193-4°; MeS, H2N, H, H, A, 150-3°; Et, H2N, H, H, A, 155°; PhCH2S, H2N, H, H, A, 178-80°; 2,4-Cl2C6H3CH2S, H2N, H, H, A, 155-7°; o-ClC6H4CH2S, H2N, Me, H, A, 143-5°; MeS, H2N, Cl, H, A, 106-8°; EtS, H2N, Cl, H, A, 109-10°; PrS, H2N, Cl, H, A, 105-6°; PrS, H2N, Me, Br, A, 95-7°; o-ClC6H4CH2S, H2N, Me, Br, A, 138-40°; p-O2NC6H4CH2S, H2N, Me, Br, A, 226-8°; EtS, H2N, EtS, H, A, 54°; PrS, H2N, PrS, H, A, 85-7°; PhCH2S, H2N, PhCH2S, H, A, 134-6°; 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, H, A, 159-61°; MeS, H2N, MeS, Ph, A, 128-9° (C7H15); PhCH2S, H2N, PhCH2S, Ph, A, 207-9° (C7H15); o-ClC6H4CH2S, H2N, o-ClC6H4CH2S, Ph, A, 174-5° (EtOAc); 2,4-Cl2C6H3CH2S, H2N, 2,4-Cl2C6H3CH2S, Ph, A, 164-7° (PhMe); MeS, MeS, Me, H, A, 43-5° (C7H15); 2,4-Cl2C6H3CH2S, MeS, Me, H, A, 100-2°; H2N, MeS, MeS, H, A, 121-3°; MeS, MeS, MeS, H, A, 114-16°; H, MeS, MeS, CO2H, B, 201-3°; PhCH2S, PhCH2S, Me, H, A, 37-9° (C7H15); o-ClC6H4CH2S, o-ClC6H4CH2S, o-ClC6H4CH2S, H, A, 117-18° (H2O-alc.); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, H, A, 94-6° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, Me, H, A, 107-9° (C7H15); H2N, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 125-7° (C7H15); 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, 2,4-Cl2C6H3CH2S, H, A, 120-4°. Other II prepared were (R, R1, R2, R3, method of synthesis, and m.p. (solvent) given): MeS, OH, H2N, H, B, 294° (H2O); MeS, H2N, Me, H, A, 152°; EtS, H2N, Me, H, A, 122-4°; BuS, H2N, Me, H, A, 70-2°; PhCH2S, H2N, Me, H, A, 118-20°; 2,4-Cl2C6H3CH2S, H2N, Me, H, A, 157-60°; p-O2NC6H4CH2S, H2N, Me, H, A, 157-9°; MeS, H2N, OH, H, B, 274-6°; EtS, H2N, OH, H, B, 248°; PrS, H2N, OH, H, B, 228-32°; BuS, H2N, OH, H, B, 240-2°; C6H11S, H2N, OH, H, B, 185°; MeS, H2N, Me, Br, A, 140-2°; PhCH2S, H2N, Me, Br, A, 135-7°; MeS, H2N, MeS, H, A, 116-18°; OH, MeS, MeS, H, B, 197° (H2O). Ultraviolet maximum at pH 1 and 11 were given for the II prepared

As far as I know, this compound(6307-44-4)Computed Properties of C5H7N3S can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 119639-24-6, is researched, Molecular C7H11NO3S, about Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation, the main research direction is palladium catalyzed cycloaddition carbon hydrogen bond activation; amide lactam cycloaddition maleimide.COA of Formula: C7H11NO3S.

Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp3)-H activation/olefin insertion would trigger a relayed, second remote C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp3)-H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity. Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) is required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes twofold C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition The initial β-C(sp3)-H activation of aliphatic amide, followed by maleimide insertion, triggers a relayed, second C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The key to success was the use of weakly coordinating amide as the directing group, as previous studies have shown that Heck or alkylation pathways are preferred when stronger-coordinating directing groups are used with maleimide coupling partners [e.g., N,N-dimethylpivalamide + N-(4-nitrophenyl)maleimide → I (87%, dr 6:1)]. To promote the amide-directed C(sp3)-H activation step, the use of pyridine-3-sulfonic acid ligands is crucial. This method is compatible with a wide range of amide substrates, including lactams, which lead to spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.

From this literature《Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation》,we know some information about this compound(119639-24-6)COA of Formula: C7H11NO3S, but this is not all information, there are many literatures related to this compound(119639-24-6).

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Tilcotil studies. [3+2]Additions with isothiazol-3(2H)-one 1,1-dioxide, the main research direction is isothiazolone dioxide regiospecific cycloaddition; tenoxicam analog; piroxicam analog; safety pyrazoloisothiazolone dioxide preparation.Application In Synthesis of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide.

Derivatives of isothiazol-3(2H)-one 1,1-dioxide (I) react regiospecifically with 1,3-dipolar agents. The main regiocontrolling factor is the C:O group of the dipolarophile. The topol. of the adducts is also in general agreement with predictions based on perturbation theory. Several adducts can be aromatized to heterocyclic equivalents of saccharin, and can then be elaborated into structural analogs of tenoxicam (Tilcotil) and piroxicam (Feldene).

From this literature《Tilcotil studies. [3+2]Additions with isothiazol-3(2H)-one 1,1-dioxide》,we know some information about this compound(119639-24-6)Application In Synthesis of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, but this is not all information, there are many literatures related to this compound(119639-24-6).

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 119639-24-6, is researched, SMILESS is O=C(C=C1)N(C(C)(C)C)S1(=O)=O, Molecular C7H11NO3SJournal, Helvetica Chimica Acta called Tilcotil studies. [3+2]Additions with isothiazol-3(2H)-one 1,1-dioxide, Author is Burri, Kaspar F., the main research direction is isothiazolone dioxide regiospecific cycloaddition; tenoxicam analog; piroxicam analog; safety pyrazoloisothiazolone dioxide preparation.Recommanded Product: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide.

Derivatives of isothiazol-3(2H)-one 1,1-dioxide (I) react regiospecifically with 1,3-dipolar agents. The main regiocontrolling factor is the C:O group of the dipolarophile. The topol. of the adducts is also in general agreement with predictions based on perturbation theory. Several adducts can be aromatized to heterocyclic equivalents of saccharin, and can then be elaborated into structural analogs of tenoxicam (Tilcotil) and piroxicam (Feldene).

From this literature《Tilcotil studies. [3+2]Additions with isothiazol-3(2H)-one 1,1-dioxide》,we know some information about this compound(119639-24-6)Recommanded Product: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, but this is not all information, there are many literatures related to this compound(119639-24-6).

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 119639-24-6, is researched, SMILESS is O=C(C=C1)N(C(C)(C)C)S1(=O)=O, Molecular C7H11NO3SJournal, Helvetica Chimica Acta called Tilcotil studies. Part 2. [4 + 2] Additions with isothiazol-3(2H)-one 1,1-dioxide, Author is Burri, Kaspar F., the main research direction is bromosiothiazole dioxide Diels Alder siloxybutadiene; oxazole isothiazolone dioxide Diels Alder; saccharin sweetening agent; pyridoisothiazole; oxicam; tilcotil; piroxicam derivative.Related Products of 119639-24-6.

The isothiazoles I (R = CMe3, CH2CO2Et, R1 = Br) are not only dipolarophiles but also reactive and versatile dienophiles, especially with oxy-substituted 1,3-butadienes, I readily combine in Diels-Alder fashion; the regiospecificity of the addition is governed by the carbonyl group of the dienophile, whereas the SO2 group can be ignored for the purpose of predicting regioselectivity. Upon dehydrobromination of the [4 + 2] adducts with DBN, the cycloaromatization process is completed, generating saccharin-like compounds Besides the parent saccharin, several hydroxylated derivatives, e.g., II (R2 = OH, R3 = H; R2 = R3 = OH) have been synthesized by this new method. II are of potential interest as non-nutritive sweetening agents. In an alternative version of this principle, the isothiazole I (R = CMe3, CH2CO2Et, CH2C6H4OMe-4, R1 = H) is reacted with the oxazole III, affording, after acid-promoted rearrangement, pyrido-annulated isothiazoles IV. Since both processes generate saccharin-related structures, they may serve in syntheses of oxicams and analogs of ipsapirone. To demonstrate the viability of the approach one representative of each series, has been converted to an oxicam.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Recommanded Product: 2-Amino-6-methylpyrimidine-4-thiol. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Amino-6-methylpyrimidine-4-thiol, is researched, Molecular C5H7N3S, CAS is 6307-44-4, about Aryl ethers of 4-[(2-hydroxyethyl)sulfanyl]pyrimidine derivatives: Pathways of synthesis and fungicidal activity of their salt forms.

2-Amino-4-[(2-aryloxyethyl)sulfanyl]-6-methylpyrimidines were obtained by S-alkylation of 2-amino-6-methylpyrimidin-4(3H)-thione with 2-aryloxyethyl chlorides. Since 2-amino-4-[(2-chloroethyl)sulfanyl]-6-methylpyrimidine is prone to in situ intramol. cyclization it cannot be used in Claisen reaction. The bromination of the target compounds provided 5-bromo derivatives; some of their hydrochlorides exhibited fungicidal activity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Park, Hojoon; Yu, Jin-Quan published the article 《Palladium-Catalyzed [3 + 2] Cycloaddition via Twofold 1,3-C(sp3)-H Activation》. Keywords: palladium catalyzed cycloaddition carbon hydrogen bond activation; amide lactam cycloaddition maleimide.They researched the compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide( cas:119639-24-6 ).Product Details of 119639-24-6. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:119639-24-6) here.

Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) is required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3 + 2] reaction that utilizes twofold C(sp3)-H activation to generate the three-carbon unit for formal cycloaddition The initial β-C(sp3)-H activation of aliphatic amide, followed by maleimide insertion, triggers a relayed, second C(sp3)-H activation to complete a formal [3 + 2] cycloaddition The key to success was the use of weakly coordinating amide as the directing group, as previous studies have shown that Heck or alkylation pathways are preferred when stronger-coordinating directing groups are used with maleimide coupling partners [e.g., N,N-dimethylpivalamide + N-(4-nitrophenyl)maleimide → I (87%, dr 6:1)]. To promote the amide-directed C(sp3)-H activation step, the use of pyridine-3-sulfonic acid ligands is crucial. This method is compatible with a wide range of amide substrates, including lactams, which lead to spiro-bicyclic products. The [3 + 2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Aryl ethers of 4-[(2-hydroxyethyl)sulfanyl]pyrimidine derivatives: Pathways of synthesis and fungicidal activity of their salt forms, published in 2016-06-30, which mentions a compound: 6307-44-4, Name is 2-Amino-6-methylpyrimidine-4-thiol, Molecular C5H7N3S, Name: 2-Amino-6-methylpyrimidine-4-thiol.

2-Amino-4-[(2-aryloxyethyl)sulfanyl]-6-methylpyrimidines were obtained by S-alkylation of 2-amino-6-methylpyrimidin-4(3H)-thione with 2-aryloxyethyl chlorides. Since 2-amino-4-[(2-chloroethyl)sulfanyl]-6-methylpyrimidine is prone to in situ intramol. cyclization it cannot be used in Claisen reaction. The bromination of the target compounds provided 5-bromo derivatives; some of their hydrochlorides exhibited fungicidal activity.

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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Synthetic Route of C5H7N3S. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Amino-6-methylpyrimidine-4-thiol, is researched, Molecular C5H7N3S, CAS is 6307-44-4, about N-(3-Sulfanylmethyl-4H-1,2,4-triazol-4-yl)-2-sulfanylacetamide Containing Terminal 2-Amino-6-methylpyrimidin-4-yl Fragments. Synthesis from 2-[(2-Amino-6-methylpyrimidin-4-yl)sulfanyl]acetohydrazide and Triethyl Orthoformate.

2-[(2-Amino-6-methylpyrimidin-4-yl)sulfanyl]acetohydrazide reacted with tri-Et orthoformate at a molar ratio of 1:1 to give 2-[(2-amino-6-methylpyrimidin-4-yl)sulfanyl]-N-{3-[(2-amino-6-methylpyrimidin-4-yl)sulfanylmethyl]-4H-1,2,4-triazol-4-yl}acetamide.

There is still a lot of research devoted to this compound(SMILES：SC1=CC(C)=NC(N)=N1)Synthetic Route of C5H7N3S, and with the development of science, more effects of this compound(6307-44-4) can be discovered.

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives》. Authors are Hambardzumyan, E. N.; Vorskanyan, A. S.; Shahbazyan, L. V.; Yengoyan, A. P..The article about the compound:2-Amino-6-methylpyrimidine-4-thiolcas:6307-44-4,SMILESS:SC1=CC(C)=NC(N)=N1).HPLC of Formula: 6307-44-4. Through the article, more information about this compound (cas:6307-44-4) is conveyed.

A series of new pyrimidine derivatives, e.g., I including those containing an azole or azine heterocycle linked through a sulfur atom or a thiomethylene group, was synthesized based on 2-amino-6-methylpyrimidine-4(3H)-thione. The synthesized compounds exhibited a pronounced stimulating effect on plants growth in the range of 43-96% compared to heteroauxin.

There is still a lot of research devoted to this compound(SMILES：SC1=CC(C)=NC(N)=N1)HPLC of Formula: 6307-44-4, and with the development of science, more effects of this compound(6307-44-4) can be discovered.

Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com