Vinylphosphonium Salt Mediated Reaction between Alkyl Propiolates and Aminophenols or Hydroxyphenols

ABSTRACT Addition of catechol to methyl propiolate or ethyl phen­ylpropiolate in the presence of Ph 3 P leads to methyl 2-(1,3-benzodioxol-2-yl)acetate or 3-(1-phenylmethylidene)-1,4-benzodioxin-2-one. 2-Aminophenols react with alkyl propiolates in the presence of Ph 3 P to produce a nearly 1:1 mixt...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-10, Vol.2006 (19), p.3243-3249
Main Authors: Yavari, Issa, Souri, Sanaz, Sirouspour, Mehdi, Djahaniani, Hoorieh
Format: Article
Language:English
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Summary:ABSTRACT Addition of catechol to methyl propiolate or ethyl phen­ylpropiolate in the presence of Ph 3 P leads to methyl 2-(1,3-benzodioxol-2-yl)acetate or 3-(1-phenylmethylidene)-1,4-benzodioxin-2-one. 2-Aminophenols react with alkyl propiolates in the presence of Ph 3 P to produce a nearly 1:1 mixture of 3-methyl-2H-1,4-benz­oxazin-2-one derivatives and methyl (E)-3-(2-aminophenoxy)-2-propenoates.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950230