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Efficient One-Pot Access to 2,9-Dihydrothiopyrano[2,3-b]indole Scaffolds Showing Large Stokes Shifts

Efficient One-Pot Access to 2,9-Dihydrothiopyrano[2,3-b]indole Scaffolds Showing Large Stokes Shifts
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摘要 A simple, mild and efficient one-pot approach for the construction of 2-aryl-3-nitro-2,9-dihydrothiopyrano- [2,3-b]indole derivatives has been realized in CH2C12 medium at ambient temperature via three-component tandem reaction of N-protected-2-chloro-3-formylindoles, sodium hydrosulfide and β-substituted nitroolefins/δ-substituted nitrodienes using DABCO (10 mol%) as an organocatalyst, followed by dehydration in the presence of activated molecular sieves (4 A). The significant advantages of this protocol are simple operation, shorter reaction time, high atom economy, good to high yields (73%-89%) and wider substrate scope. In addition, all the synthesized com- pounds have shown the large positive Stokes shift values (5632-6081 cm ^-1). A simple, mild and efficient one-pot approach for the construction of 2-aryl-3-nitro-2,9-dihydrothiopyrano- [2,3-b]indole derivatives has been realized in CH2C12 medium at ambient temperature via three-component tandem reaction of N-protected-2-chloro-3-formylindoles, sodium hydrosulfide and β-substituted nitroolefins/δ-substituted nitrodienes using DABCO (10 mol%) as an organocatalyst, followed by dehydration in the presence of activated molecular sieves (4 A). The significant advantages of this protocol are simple operation, shorter reaction time, high atom economy, good to high yields (73%-89%) and wider substrate scope. In addition, all the synthesized com- pounds have shown the large positive Stokes shift values (5632-6081 cm ^-1).
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2015年第11期1244-1250,共7页 中国化学(英文版)
关键词 one-pot MCR 2 9-dihydrothiopyrano[2 3-b]indole ORGANOCATALYSIS molecular sieves large Stokes shifts one-pot MCR, 2,9-dihydrothiopyrano[2,3-b]indole, organocatalysis, molecular sieves, large Stokes shifts
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