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Synthesis 2016; 48(08): 1235-1245
DOI: 10.1055/s-0035-1561376
DOI: 10.1055/s-0035-1561376
paper
A Five-Step Cascade for the Modular and Regiodefined Synthesis of Naphth[2,1-d]oxazoles
Further Information
Publication History
Received: 30 September 2015
Accepted after revision: 14 January 2016
Publication Date:
16 February 2016 (online)
◊ These authors have contributed equally to this work.
Abstract
The reaction of 3-nucleofugal phthalides with 2-amidoacrylates is shown to provide a synthesis of densely substituted naphth[2,1-d]oxazoles in good yields. It is proposed to proceed via a five-step cascade which includes phthalide annulation, demethoxycarbonylation, and heterocyclization. The methodology is free from regiochemical ambiguity of the products. In certain cases, the corresponding 2-amidonaphthoquinones are directly formed.
Key words
demethoxycarbonylative annulation - naphth[2,1-d]oxazoles - phthalides - cascade - heterocyclesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561376.
- Supporting Information
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