Jump to main content
Jump to site search

Issue 29, 2020
Previous Article Next Article

Synthesis of cyclopentaquinolinone and cyclopentapyridinone from ortho-alkynyl-N-arylaldehyde via superbase-promoted C–N, C–O and C–C bond formation

Author affiliations

Abstract

An environmentally benign, transition metal-free, superbase-mediated intramolecular annulation of o-alkynylaldehydes with primary amines forms highly functionalized amino-substituted cyclopentaquinolinones and cyclopentapyridinones via C–N, C–C, and C[double bond, length as m-dash]O bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray crystallographic studies support the assigned structures of the amino-fused N-heterocycles.

Graphical abstract: Synthesis of cyclopentaquinolinone and cyclopentapyridinone from ortho-alkynyl-N-arylaldehyde via superbase-promoted C–N, C–O and C–C bond formation

Back to tab navigation

Supplementary files

Article information


Submitted
22 Jun 2020
Accepted
30 Jun 2020
First published
03 Jul 2020

Org. Biomol. Chem., 2020,18, 5594-5601
Article type
Paper

Synthesis of cyclopentaquinolinone and cyclopentapyridinone from ortho-alkynyl-N-arylaldehyde via superbase-promoted C–N, C–O and C–C bond formation

K. M. Saini, R. K. Saunthwal, Sushmita and A. K. Verma, Org. Biomol. Chem., 2020, 18, 5594
DOI: 10.1039/D0OB01281E

Social activity

Search articles by author

Spotlight

Advertisements