期刊
NEW JOURNAL OF CHEMISTRY
卷 46, 期 38, 页码 18505-18511出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj03719j
关键词
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资金
- Central Washington University
- School of Graduate Studies and Research
- Office of Undergraduate Research (OUR)
- Organic Syntheses, Inc
- Provost Denbeste
This study reveals that dithiodiglycolic anhydride can undergo formal cycloaddition with aryl aldimines to yield functionalized 4-thiazolidinones. 2-alkenyl-4-thiazolidinones can be obtained when 1,3-azadienes are used. These compounds serve as the core structure of various pharmaceuticals with diverse biological activities.
Cyclic anhydrides, including sulfur-embedded anhydrides such as thiodiglycolic anhydride, are useful dipolar synthons for the synthesis of complex organic molecules through formal cycloaddition reactions with imines (i.e., the Castagnoli-Cushman Reaction (CCR)). Here, we disclose that a disulfide-embedded anhydride (i.e., dithiodiglycolic anhydride) unexpectedly underwent an efficient formal cycloaddition with aryl aldimines to afford functionalized 4-thiazolidinones, without complications arising from the CCR. Importantly, when 1,3-azadienes were employed, the 2-alkenyl-4-thiazolidinones were obtained without complications stemming from the sulfa-Michael reaction or the Tamura reaction. These 4-thiazolidinones constitute the core of several pharmaceuticals that display a broad spectrum of biological activities, including anti-HIV and anticancer. The current tactic obviates the need for thioglycolic acid, an alternative annulation partner associated with a strongly unpleasant odor. The ensuing N,S-heterocycles are then engaged in several selective fragment growth processes, including oxidation to sulfoxides, sulfones, and epoxysulfones.
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