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Issue 5, 2015
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Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

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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

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Publication details

The article was received on 28 Oct 2014, accepted on 26 Nov 2014 and first published on 26 Nov 2014


Article type: Paper
DOI: 10.1039/C4OB02286F
Org. Biomol. Chem., 2015,13, 1521-1530

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    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

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