期刊
SYNTHESIS-STUTTGART
卷 54, 期 6, 页码 1613-1620出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1693-7535
关键词
beta-ketothioamides; AIBN; domino annulation; one-pot reaction; 1, 3-thiazolidin-4-ones
资金
- Science and Engineering Research Board (SERB), New Delhi [CRG/2019/000058]
- University Grants Commission (UGC), Institutes of Eminence (IoE) Incentive Grant [6031]
- Council of Scientific and Industrial Research, New Delhi [02(0348)/19/EMR-II]
- JC Bose National Fellowship, New Delhi [JCB/2020/000023]
This study presents an efficient copper-catalyzed intermolecular radical [3+2] annulation of thioamides with AIBN, allowing for the synthesis of thiazolidin-4-ones in good yields. The reaction is operationally simple and the products exhibit an asymmetric stereochemistry.
An efficient and versatile copper-catalyzed intermolecular radical [3+2] annulation of thioamides with azobisisobutyronitrile (AIBN) is described. This two-component copper(II)-catalyzed transformation is achieved in one pot via cascade formation of C-S/C-N bonds through cyclization of an in situ generated N,S-acetal intermediate derived from a.-ketothioamide. This operationally simple method allows direct access to synthetically demanding thiazolidin-4-ones in good to excellent yields containing diverse functional groups of different electronic and steric nature. The readily available reaction partners, the avoidance of expensive/toxic reagents and a gram-scale synthesis are additional attributes of this strategy. AIBN plays a dual role as a radical initiator and an unusual source of a two-carbon coupling partner. Notably, the products possess Z stereochemistry with regard to the exocyclic C=C double bond at position 2 of the thiazolidine ring.
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