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Efficient Synthesis of [1,3]Oxazino[3,2‐ f ]phenanthridine Derivatives by a Novel 1,4‐Dipolar Cycloaddition Involving a Phenanthridine–Dimethyl Acetylenedicarboxylate Zwitterion and Aromatic Aldehydes
Author(s) -
Li Ming,
Pan Lei,
Wen LiRong
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000165
Subject(s) - phenanthridine , chemistry , dimethyl acetylenedicarboxylate , cycloaddition , zwitterion , 1,3 dipolar cycloaddition , medicinal chemistry , organic chemistry , molecule , catalysis
An efficient synthesis of [1,3]oxazino[3,2‐ f ]phenanthridine derivatives via a three‐component reaction of phenanthridine, dimethyl acetylenedicarboxylate (DMAD), and aromatic aldehydes is described. This novel method is complementary to the classical Huisgen 1,4‐dipolar cycloaddition in that it is well‐suited to the preparation of [1,3]oxazino[3,2‐ f ]phenanthridines.