Silver(i)-catalyzed sequential hydroamination and Prins type cyclization for the synthesis of fused benzo-δ-sultams

An intramolecular annulation strategy has been developed for the synthesis of tetrahydrobenzo[e]pyrano[4,3-c][1,2]thiazine derivatives by means of coupling of aldehydes with 2-(4-hydroxybut-1-yn-1-yl)-N-arylsulfonamides using a catalytic amount of silver hexafluoroantimonate in toluene at 80 °C. Thi...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (28), p.5163-5166
Main Authors: Maheshwar Rao, B, Yadav, J S, Sridhar, B, Subba Reddy, B V
Format: Article
Language:English
Subjects:
Aldehydes
Catalysis
Chemical reactions
Chemical synthesis
Derivatives
Organic chemistry
Silver
Toluene
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Summary:An intramolecular annulation strategy has been developed for the synthesis of tetrahydrobenzo[e]pyrano[4,3-c][1,2]thiazine derivatives by means of coupling of aldehydes with 2-(4-hydroxybut-1-yn-1-yl)-N-arylsulfonamides using a catalytic amount of silver hexafluoroantimonate in toluene at 80 °C. This is the first report on the synthesis of fused benzo-δ-sultam derivatives through C-N, C-O, and C-C bond formations. The reaction proceeds through a cascade of hydroamination and Prins type cyclization.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00918j