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Issue 28, 2018
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Silver(i)-catalyzed sequential hydroamination and Prins type cyclization for the synthesis of fused benzo-δ-sultams

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Abstract

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.

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

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Supplementary files

Article information


Submitted
19 Apr 2018
Accepted
24 Jun 2018
First published
25 Jun 2018

Org. Biomol. Chem., 2018,16, 5163-5166
Article type
Paper

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

B. Maheshwar Rao, J. S. Yadav, B. Sridhar and B. V. Subba Reddy, Org. Biomol. Chem., 2018, 16, 5163
DOI: 10.1039/C8OB00918J

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