Publication
Title
Guanidine synthesis : use of amidines as guanylating agents
Author
Abstract
The use of amidines for the tandem or one pot synthesis of guanidines is reported. Guanidines are obtained by oxidative rearrangement of readily available and stable amidines into carbodiimides, followed by in situ reaction with amines. The protocol can be executed under mild reaction conditions (30°C), in a green solvent (dimethyl carbonate). The amine scope is broad, including sterically hindered, oxidation sensitive and chiral amines. Examples for the synthesis of both acyclic and cyclic guanidines are provided. 2-PrOPhI byproduct, generated from the oxidant 2-PrOPhINTs, can be isolated in high yields making regeneration of the hypervalent iodine reagent possible. The utility and greenness of the synthetic method is demonstrated by a new route towards the antihypertensive drug Pinacidil. The Process Mass Intensity (PMI) of the new route is only 24% of the classical one.
Language
English
Source (journal)
Advanced synthesis and catalysis. - Weinheim
Publication
Weinheim : 2016
ISSN
1615-4150
Volume/pages
358:5(2016), p. 826-833
ISI
000372132100018
Full text (Publisher's DOI)
Full text (open access)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 04.02.2016
Last edited 16.06.2017
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