The Reaction of Acyloxysulfonium Salt with Cyclic Enol Ethers: Novel Synthesis of Vinyl Sulfides

Jain, Sanjay; Shukla, Krupa H.; Mukhopadhyay, A.; Suryawanshi, S. N.; Bhakuni, D. S.

doi:10.1080/00397919008052843

Cited by 45 publications

(37 citation statements)

References 8 publications

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“…The 1 H), 7.23 (t, J = 7.5 Hz, 2 H), 7.14 (t, J = 7.5 Hz, 1 H), 7.08-7.06 (m, 2 H), 6.82 (d, J = 4.5 Hz, 1 H). 13 C NMR (125 MHz, CDCl 3 ): δ = 152.7, 151.5, 135. 9, 133.6, 129.5, 128.5, 128.2, 127.6, 126.2, 125.9, 118.1, 113.1, 107.8. LRMS (EI, 70 eV): m/z (%) = 308 (65), 188 (12), 187 (100), 121 (10), 51 (6).…”

Section: -Phenyl-5-(phenylthio)imidazo[21-b]thiazole (3aa); 20d Typmentioning

confidence: 99%

“…13 C NMR (125 MHz, CDCl 3 ): δ = 158.7, 151. 9,151.1,133.7,128.6,128.4,128.1,127.6,126.2,118.1,115.2,112.9,109.5,55.4.…”

Section: -[(4-methoxyphenyl)thio]-6-phenylimidazo[21-b]thiazole (3ac)mentioning

confidence: 99%

“…(d, J = 4.4 Hz, 1 H). 13 C NMR (125 MHz, CDCl 3 ): δ = 153. 6, 152.2, 138.5, 135.8, 133.7, 130.9, 128.9, 128.8, 127.9, 126.8, 125.9, 124.2, 118.3, 113.7, 107. …”

Section: -[(3-chlorophenyl)thio]-6-phenylimidazo[21-b]thiazole (3ad)mentioning

confidence: 99%

“…9,151.1,133.7,128.6,128.4,128.1,127.6,126.2,118.1,115.2,112.9,109.5,55.4. LRMS (EI,70 eV): m/z (%) = 338 (66), 188 (13), 187 (100), 152 (4) …”

Section: -[(4-methoxyphenyl)thio]-6-phenylimidazo[21-b]thiazole (3ac)mentioning

confidence: 99%

“…10 In recent years, direct sulfenylation of heterocyclic compounds has become an intriguing strategy for the synthesis of biological molecules. Significant progress in the direct sulfenylation of indoles has been made using various sulfenylating agents such as sulfenyl halides, 11 N-thioimides, 12 sulfonium salts, 13 thiols, 14 disulfides, 15 quinone mono-O,S-acetals, 16 arenesulfonyl chlorides, 17 and sulfonyl hydrazides. 18 However, little attention has been paid to the direct sulfenylation of imidazoheterocycles.…”

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Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

Zhou

Chen

et al. 2015

Synthesis

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Imidazoheterocycles undergo efficient and regioselective sulfenylation with disulfides using the iodine/hydrogen peroxide system in ethanol at 25 °C. This green strategy tolerates a wide range of functional groups to afford diverse sulfenylated imidazoheterocycles in high yields. Moreover, the fipronil (a pesticide) skeleton can be readily attached to imidazoheterocycles using this strategy, which is significant in drug development.The functionalization of imidazoheterocycles is an important task for biochemists and synthetic chemists because imidazoheterocyclic motifs are privileged scaffolds that exhibit a broad range of biological activity. 1 For example, imidazo[2,1-b]thiazoles exhibit good activity as anticancer agents, 2 SIRT1 activators, 3 RSK2 inhibitors, 4 and antiviral agents, 5 and in the treatment of cystic fibrosis. 6 Several drugs (including alpidem, olprinone, necopidem, zolimidine, and saripidem) have been developed by functionalization of the imidazo[1,2-a]pyridine skeleton. 7 As a result, substantial efforts have been devoted to the functionalization of imidazoheterocycles. 8,9 Sulfenyl groups are important structural units in many naturally occurring and bioactive compounds. 10 In recent years, direct sulfenylation of heterocyclic compounds has become an intriguing strategy for the synthesis of biological molecules. Significant progress in the direct sulfenylation of indoles has been made using various sulfenylating agents such as sulfenyl halides, 11 N-thioimides, 12 sulfonium salts, 13 thiols, 14 disulfides, 15 quinone mono-O,S-acetals, 16 arenesulfonyl chlorides, 17 and sulfonyl hydrazides. 18 However, little attention has been paid to the direct sulfenylation of imidazoheterocycles. 9t,15c,19-21 The present metal-free methods suffer from some drawbacks such as using corrosive acid, 20b a commercially unavailable ionic liquid, 20c or excess N-chlorosuccinimide. 20d Major limitations in scaling up reactions arise from metal pollution, and the use of harsh reaction conditions and excess reagents. During this work, Hiebel et al. 21 developed an efficient method for the sulfenylation of imidazoheterocycles with thiophenols using iodine as a catalyst in PEG 400 . However, a higher reaction temperature is required to resolve the solubility problems of some starting materials in PEG 400 . These sulfenylation methodologies mainly focus on imidazo[1,2-a]pyridines, whereas the sulfenylation of imidazo[2,1-b]thiazoles remains scarce. 20d The development of a highly efficient, ecofriendly, practical, and applicable method for the sulfenylation of imidazo[2,1-b]thiazoles is highly desirable. We hypothesized that catalytic amount of elemental iodine would accomplish the sulfenylation of imidazoheterocycles with disulfides in the presence of hydrogen peroxide. Moreover, disulfides are desirable sulfenylating agents as they are less toxic and more stable than thiols. As a part of our continuing interest in direct C-H sulfenylation, 15b,22 we report an iodine/hydrogen peroxide-promoted regioselective sulf...

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Section: -Phenyl-5-(phenylthio)imidazo[21-b]thiazole (3aa); 20d Typmentioning

confidence: 99%

“…13 C NMR (125 MHz, CDCl 3 ): δ = 158.7, 151. 9,151.1,133.7,128.6,128.4,128.1,127.6,126.2,118.1,115.2,112.9,109.5,55.4.…”

Section: -[(4-methoxyphenyl)thio]-6-phenylimidazo[21-b]thiazole (3ac)mentioning

confidence: 99%

“…(d, J = 4.4 Hz, 1 H). 13 C NMR (125 MHz, CDCl 3 ): δ = 153. 6, 152.2, 138.5, 135.8, 133.7, 130.9, 128.9, 128.8, 127.9, 126.8, 125.9, 124.2, 118.3, 113.7, 107. …”

Section: -[(3-chlorophenyl)thio]-6-phenylimidazo[21-b]thiazole (3ad)mentioning

confidence: 99%

“…9,151.1,133.7,128.6,128.4,128.1,127.6,126.2,118.1,115.2,112.9,109.5,55.4. LRMS (EI,70 eV): m/z (%) = 338 (66), 188 (13), 187 (100), 152 (4) …”

Section: -[(4-methoxyphenyl)thio]-6-phenylimidazo[21-b]thiazole (3ac)mentioning

confidence: 99%

mentioning

confidence: 99%

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Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

Zhou

Chen

et al. 2015

Synthesis

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Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions

et al. 2001

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The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)2]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating O-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.

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Vinyl sulfides

Трофимов¹,

Shainyan²

1993

PATAI'S Chemistry of Functional Groups

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The Reaction of Acyloxysulfonium Salt with Cyclic Enol Ethers: Novel Synthesis of Vinyl Sulfides

Cited by 45 publications

References 8 publications

Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions

Vinyl sulfides

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