Solid-Phase Synthesis of 1,3,5,6-Tetra-Substituted 3,5-Dihydroimidazo[4,5-c][1,2]Thiazin-4(1 H)-One 2,2-Dioxide Derivatives

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2025-07-30 DOI:10.1002/jhet.70045

Jimin Moon, Hyojin Lee, Sohee Kim, Taeho Lee

引用次数: 0

Abstract

The synthesis of 1,3,5,6-tetra-substituted 3,5-dihydroimidazo[4,5-c][1,2]thiazin-4(1H)-one 2,2-dioxide derivatives was optimized through solid-phase synthesis. Synthetic strategies such as Merrifield resin, Thorpe-Ziegler reaction, Mitsunobu reaction, intramolecular cyclization, and desulfonative nucleophilic substitution were employed to synthesize a total of 31 derivatives. The synthesis showed high yields of 72%–87% per step over 8 steps, resulting in an overall yield of 7%–33%, thereby developing an efficient synthetic route for the derivatives.

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1,3,5,6-四取代3,5-二氢咪唑[4,5-c][1,2]噻嗪-4(1 H)- 1 2,2-二氧化物衍生物的固相合成

采用固相合成法优化了1,3,5,6-四取代3,5-二氢咪唑[4,5-c][1,2]噻嗪-4(1H)- 1 2,2-二氧化物衍生物的合成。采用Merrifield树脂、Thorpe-Ziegler反应、Mitsunobu反应、分子内环化、脱硫亲核取代等合成策略，共合成了31个衍生物。经过8步合成，每步产率高达72% ~ 87%，总产率为7% ~ 33%，为该衍生物的合成开辟了一条高效的路线。

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.