Transition-Metal-Free TBAI-Facilitated Addition–Cyclization of N‑Methyl‑N‑arylacrylamides with Arylaldehydes or Benzenesulfonohydrazides: Access to Carbonyl- and Sulfone-Containing N‑Methyloxindoles
A highly efficient addition–cyclization of N-methyl-N-arylacrylamides with arylaldehydes or benzenesulfonohydrazides was developed using a catalytic amount of the quaternary ammonium salt (TBAI) under metal-free conditions, leading to the carbonyl- and sulfone-containing oxindoles. Compared to pre...
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Published in | Journal of organic chemistry Vol. 81; no. 12; pp. 5181 - 5189 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.06.2016
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A highly efficient addition–cyclization of N-methyl-N-arylacrylamides with arylaldehydes or benzenesulfonohydrazides was developed using a catalytic amount of the quaternary ammonium salt (TBAI) under metal-free conditions, leading to the carbonyl- and sulfone-containing oxindoles. Compared to previous methods, which require excessive amounts of explosive organic peroxides and precious or toxic metal reagents, the present protocol, which gave access to 3,3-disubstituted oxindoles, is a safe and green approach, resulting in the formation of various useful carbonyl- and sulfone-containing oxindoles in yields of 40–94%. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b00773 |