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  • Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes for the synthesis of cyclopenta[c]chromene skeletons.

Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes for the synthesis of cyclopenta[c]chromene skeletons.

Chemistry, an Asian journal (2012-04-11)
Xiao-Feng Xia, Xian-Rong Song, Xue-Yuan Liu, Yong-Min Liang
ABSTRACT

An efficient method to construct cyclopenta[c]chromene skeletons by Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes is presented. Two new fused cycles can be formed in one step in moderate to excellent yields (up to 94 %), and the products can be converted into bioactive barbituric acid derivatives (1) under simple reaction conditions.

MATERIALS
Product Number
Brand
Product Description

Supelco
Barbituric acid, for spectrophotometric det. of cyanide, ≥99.5%
Sigma-Aldrich
Barbituric acid, ReagentPlus®, 99%
Sigma-Aldrich
Sodium barbiturate, ≥97.0% (T)