Domino-Annulation-Based Approach to Synthesize Bridged Bis-thiopyrano[2,3-b]indoles and Unbridged
Yan-Hui Fu1, Chun Zhang1,2, Wei Xu2
1Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China.
Abstract:
A novel domino strategy for the construction of intricate bridged bis-thiopyrano[2,3-b]indoles was disclosed, which involved one molecule of 3-formylchromones and two molecules of indoline-2-thiones, enabling the formation of four new bonds in a single operation. The transformation occurred under mild reaction conditions, facilitated by the synergistic action of the base NaHCO3 and the catalytic acid ZnCl2. Notably, when these bridged bis-thiopyrano[2,3-b]indole skeletons were treated with alkyl halides under basic conditions, they underwent deconstruction to yield alkylthio-substituted indole-decorated thiopyrano[2,3-b]indoles.
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