Catalyst-free anti-Markovnikov hydroamination and hydrothiolation of vinyl heteroarenes in aqueous medium: an improved process towards centhaquine.
Org Biomol Chem
; 22(8): 1721-1726, 2024 Feb 21.
Article
em En
| MEDLINE
| ID: mdl-38318984
ABSTRACT
Catalyst-free hydroamination and hydrothiolation of alkenes have been achieved in an aqueous medium. The anti-Markovnikov addition works efficiently in suspended water at room temperature and allows straightforward access to centhaquine, a drug used for the management of hypovolemic shocks in critically ill patients, and its derivatives. Various primary and secondary amines, thiols, and hydrazides were successfully reacted with a number of heteroaryl/aryl-alkenes. The scalability of the process has been demonstrated by synthesizing centhaquine at a 19.65 g scale. A comparative analysis of the present process with previous approaches has been provided on the basis of green chemistry metrics.
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MEDLINE
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En
Ano de publicação:
2024
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Article