Phosphazene-Base-Catalyzed Tandem Addition-Cyclization Reaction of o-Alkynylbenzaldehyde with Oxygen and Nitrogen Nucleophiles

The tandem addition-cyclization reaction between o-alkynylbenzaldehyde and nucleophile catalyzed by P4-'Bu, a phosphazene base, is demonstrated. The nucleophilic cyclization is efficiently triggered not only by alcohols, including sterically demanding ones, but also by nitrogen nucleophiles, su...

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Bibliographic Details
Published inSynlett no. 4; pp. 638 - 642
Main Authors Kanazawa, Chikashi, Ito, Akira, Terada, Masahiro
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
o-alkynylbenzaldehyde
CARBONYL GROUPS
LEWIS-ACID
ALKYNES
cyclization
2-ALKYNYLBENZALDEHYDES
ORGANIC-BASE
INTRAMOLECULAR CYCLIZATION
VERSATILE
phosphazene
CYCLIC ALKENYL ETHERS
POLYAMINOPHOSPHAZENES
isobenzofuran
ADDITION/CYCLIZATION
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Summary:The tandem addition-cyclization reaction between o-alkynylbenzaldehyde and nucleophile catalyzed by P4-'Bu, a phosphazene base, is demonstrated. The nucleophilic cyclization is efficiently triggered not only by alcohols, including sterically demanding ones, but also by nitrogen nucleophiles, such as amide and pyrrole, under the influence of a catalytic amount of P4-'Bu. The method enables efficient access to isobenzofuran derivatives under mild conditions.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0028-1087909