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Synthesis 2013; 45(24): 3349-3354
DOI: 10.1055/s-0033-1340040
DOI: 10.1055/s-0033-1340040
paper
Copper-Catalyzed Domino Synthesis of Quinazolin-4(3H)-ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide
Weitere Informationen
Publikationsverlauf
Received: 21. August 2013
Accepted after revision: 23. September 2013
Publikationsdatum:
18. Oktober 2013 (online)
Abstract
Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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