Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids-Reference-Cited by-同舟云学术

Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

Published:2021-03-24 Issue:7-8 Volume:45 Page:674-678
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Sekgota Khethobole C¹,Isaacs Michelle²,Hoppe Heinrich C²³,Seldon Ronnett⁴,Warner Digby F⁵,Khanye Setshaba D²⁶,Kaye Perry T¹²^ORCID

Affiliation:

1. Department of Chemistry, Rhodes University, Makhanda/Grahamstown, South Africa

2. Centre for Chemico- and Biomedicinal Research, Rhodes University, Makhanda/Grahamstown, South Africa

3. Department of Biochemistry and Microbiology, Rhodes University, Makhanda/Grahamstown, South Africa

4. Drug Discovery and Development Centre (H3-D), Department of Chemistry, University of Cape Town, Cape Town, South Africa

5. SAMRC/NHLS/UCT Molecular Mycobacteriology Research Unit, Department of Pathology and Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Cape Town, South Africa

6. Division of Pharmaceutical Chemistry, Faculty of Pharmacy, Rhodes University, Makhanda/Grahamstown, South Africa

Abstract

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.1177/1747519820987156

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