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One-Pot Synthesis of Functionalized 2H-Chromene (=2H-1-Benzopyran) Derivatives via a Three-Component Reaction between a CH-Acid, a Dialkyl Acetylenedicarboxylate, and Methyl Chloroglyoxylate or Benzyl Carbonochloridate Mediated by Triphenylphosphine

✍ Scribed by Mohammad Bayat; Nader Zabarjad Shiraz; Soheila Shafei Asayesh

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
165 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

An effective route to functionalized 2__H__‐chromene (=2__H__‐1‐benzopyran) derivatives 4 is described (Scheme 1). This involves the reaction of a 1,1‐diactivated alkene, resulting from the reaction of dimedone (=5,5‐dimethylcyclohexane‐1,3‐dione; 1a) with methyl chloroglyoxylate (ClC(O)COOMe), benzyl carbonochloridate (ClC(O)OCH~2~Ph) or 3,5‐dinitrobenzoyl chloride (3,5‐(NO~2~)~2~C~6~H~3~C(O)Cl), and a dialkyl acetylenedicarboxylate (=dialkyl but‐2‐ynedioate) in the presence of Ph~3~P which undergo intramolecular Wittig reaction to produce 2__H__‐chromene derivatives (Scheme 1).

📜 SIMILAR VOLUMES

ChemInform Abstract: One-Pot Synthesis o
ChemInform Abstract: One-Pot Synthesis of Functionalized 2H-Chromene (=2H-1-Benzopyran) Derivatives via a Three-Component Reaction Between a CH-Acid, a Dialkyl Acetylenedicarboxylate, and Methyl Chloroglyoxylate or Benzyl Carbonochloridate Mediated by Triphenylphosphine.
✍ Mohammad Bayat; Nader Zabarjad Shiraz; Soheila Shafei Asayesh 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 27 KB 👁 2 views

## Abstract The title process is based on the initial formation of a reactive 1,1‐diactivated alkene from dimedone or dimethylbarbituric acid and carbonyl compounds (II) followed by a intramolecular Wittig‐type ring closure.