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- Title
Successful utilization of β-ketonitrile in Biginelli reaction: synthesis of 5-cyanodihydropyrimidine.
- Authors
Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam
- Abstract
Abstract: A Biginelli reaction of β<inline-graphic></inline-graphic>-ketonitriles, aldehydes and urea in principle can yield 5-cyano substituted dihydropyrimidinones. Although potentially very useful, this substituted heterocycle is often difficult to synthesize via the three component reaction, presumably due to the lack of stability of β<inline-graphic></inline-graphic>-ketonitriles. The present work describes the development of reaction conditions yielding the desired product. Interesting mechanistic observations have also been noted. Thirteen new compounds (derivatives) of 5-cyanodihydropyrimidin were synthesized.GRAPHICAL ABSTRACT: Synopsis A straightforward and efficient multicomponent Biginelli reaction employing β<inline-graphic></inline-graphic>-ketonitrile with aromatic or non-enolizable aliphatic aldehydes and urea in the presence of CuCl to cyano substituted dihydropyrimidones has been developed. A detailed study has been carried out to understand the reaction kinetics and an appropriate reaction mechanism has been proposed. <graphic></graphic>
- Subjects
NITRILE derivatives; PYRIMIDINE derivatives; PYRIMIDINE synthesis; SUBSTITUTION reactions; HETEROCYCLIC compounds
- Publication
Journal of Chemical Sciences, 2018, Vol 130, Issue 6, p1
- ISSN
0974-3626
- Publication type
Article
- DOI
10.1007/s12039-018-1467-7