Effective and Catalyst-Free Preparation of Thiazolidines via Novel [3<bold>+</bold>2] Annulation of 1,4-Dithiane-2,5-diol and Benzothiazolimines

被引：0

作者：

Liu, Min ^{[1
]}

Zhao, Lin-quan ^{[1
]}

Song, Xiang-jia ^{[1
]}

Lu, Jin-rong ^{[1
]}

Cui, Wen-quan ^{[1
]}

机构：

[1] North China Univ Sci & Technol, Coll Chem Engn, Tangshan 063210, Peoples R China

来源：

SYNLETT | 2025年

关键词：

3+2] annulation; 1,4-dithiane-2,5-diol; benzothiazolimines; thiazolidines; ADMET; ASYMMETRIC-SYNTHESIS; DERIVATIVES; BEARING; ACCESS;

D O I：

10.1055/a-2509-5433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel [3+2] annulation of 1,4-dithiane-2,5-diol and benzothiazolimines has been developed for the efficient, one-step preparation of highly sterically demanding thiazolidines in excellent yields (up to 99%) and moderate diastereoselectivities (1:1 to 2.4:1) under mild conditions within a few minutes. A series of thiazolidines compounds were obtained and a scaled-up experiment was conducted with excellent results. The absorption, metabolism, and toxic (ADMET) properties of the compounds were evaluated with good results, demonstrating the potential applications of this protocol.

引用

页数：4

共 14 条

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[2] Synthesis of 2-Substituted-4,5-Dihydrothiazol-4-Ols by [3+2] Annulation of 1,4-Dithiane-2,5-Diol with Thioamides
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[3] Facile preparation of 3,5-disubstituted-4-aminothiophene-2-carbaldehyde from a novel unexpected domino reaction of vinyl azides and 1,4-dithiane-2,5-diol
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[4] Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol
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[5] Facile one-pot synthesis of 2,3-thienoimides via formal [3+2] annulation reaction of 1,4-dithiane-2,5-diol and N-substituted imides
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[6] I2-DMSO-mediated formal [3+1+2] synthesis of pyrimido[1,2-b] indazole using 1,4-dithiane-2,5-diol as a surrogate of ethylene
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[7] Acetic Acid Mediated Regioselective [3+3] Cycloaddition of Substituted Cyclopropane-1,1-dicarbonitriles with 1,4-Dithiane-2,5-diol
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[8] Base catalyzed reaction of 1,4-dithiane-2,5-diol with α-oxoketene dithioacetals: a new general method for the synthesis of 2-methylthio-3-aroyl/heteroaroyl thiophenes
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[9] 1,4-Dithiane-2,5-diol as an efficient synthon for a straightforward synthesis of functionalized tetrahydrothiophenes via sulfa-Michael/aldol-type reactions with electrophilic alkenes
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[10] Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes via in Situ Generated Chiral Fluoride-Catalyzed Cascade Sulfa-Michael/Aldol Reaction of 1,4-Dithiane-2,5-diol and α,β-Unsaturated Ketones
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