Jump to main content
Jump to site search


An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies

Author affiliations

Abstract

A serendipitous discovery of [1,3]-sulfonyl migration has been made in the two-component reaction of azomethine imine and allenoates. Current methodology involving N–S bond cleavage and C–S bond formation provided easy access to biologically important arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazolines. Subsequently, a one-pot sequential protocol has been developed from the easily available starting material. The mechanistic investigation using quantum chemical methods revealed that the sulfonyl migration step is a concerted [1,3]-sigmatropic shift.

Graphical abstract: An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Aug 2019, accepted on 14 Nov 2019 and first published on 14 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC06751E
Chem. Commun., 2019, Advance Article

  •   Request permissions

    An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies

    A. J. Ansari, A. A. Wani, A. K. Maurya, S. Verma, V. K. Agnihotri, A. Sharon, P. V. Bharatam and D. M. Sawant, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06751E

Search articles by author

Spotlight

Advertisements