Issue 5, 2015

Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

Abstract

An efficient palladium-catalyzed tandem approach for the synthesis of highly functionalized tetrahydroquinazolines 4a–q, and 5a–f by the reaction of o-haloanilines 1a–g with acrylates 2a–d and isothiocyanates 3aa–3ah/isocyanates 3ba–3bfvia Heck-conjoined amidation/thioamidation and concomitant chemoselective Michael-addition is described. A competitive experiment showed that isothiocyanates were more reactive than isocyanates. The developed methodology offers an efficient chemoselective process for the synthesis of highly functionalized tetrahydroquinazolines under mild and operationally simple reaction conditions from inexpensive and commercially available starting substrates.

Graphical abstract: Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

Supplementary files

Article information

Article type
Paper
Submitted
28 Oct 2014
Accepted
26 Nov 2014
First published
26 Nov 2014

Org. Biomol. Chem., 2015,13, 1521-1530

Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

R. K. Saunthwal, M. Patel, A. K. Danodia and A. K. Verma, Org. Biomol. Chem., 2015, 13, 1521 DOI: 10.1039/C4OB02286F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements