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Gold-catalyzed domino cycloisomerization/Pictet-Spengler reaction of 2-(4-aminobut-1-yn-1-yl)anilines with aldehydes: synthesis of tetrahydropyrido[4,3-b]indole scaffolds.

Authors
  • Subba Reddy, B V
  • Swain, Manisha
  • Reddy, S Madhusudana
  • Yadav, J S
  • Sridhar, B
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Dec 21, 2012
Volume
77
Issue
24
Pages
11355–11361
Identifiers
DOI: 10.1021/jo302068e
PMID: 23205599
Source
Medline
License
Unknown

Abstract

A domino cycloisomerization/Pictet-Spengler reaction of 2-(4-aminobut-1-yn-1-yl)aniline with aldehydes has been achieved using a AuIPrCl (5 mol %)/AgSbF(6) (10 mol %) catalytic system to produce the corresponding 1-aryl-N-tosyl-2,3,4,5-tetrahydropyrido[4,3-b] indole derivatives in good yields. This is the first report on the synthesis of tetrahydro pyrido[4,3-b]indole scaffolds through as tandem 5-endo-dig cyclization and Pictect-Spengler reaction.

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