Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles: a new entry to [1,4]oxazino[4,3- a]indoles

The unusual [1,4]oxazino[4,3- a]indole nucleus was prepared, under mild reaction conditions, by reacting 1-alkynyl-1 H-indole-2-carbaldehydes with various alkoxides, generated in situ from the corresponding alkyl, benzyl, allyl and propargyl alcohols.

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 42; pp. 7117 - 7120
Main Authors Abbiati, Giorgio, Canevari, Valentina, Caimi, Solange, Rossi, Elisabetta
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.10.2005
Elsevier
Subjects
1-Alkynyl-1 H-indole-2-carbaldehydes
[1,4]Oxazino[4,3- a]indole
Alcohol
Chemistry
Chemistry, Organic
Domino addition/annulation
Physical Sciences
Science & Technology
Sodium
1-Alkynyl-1 H-indole-2-carbaldehydes
Alcohol
Sodium
Domino addition/annulation
[1,4]Oxazino[4,3- a]indole
alcohol
ACETYLENIC ALDEHYDES
[1,4]oxazino[4,3-a]-indole
QUINOLINES
CATALYST
ALKYNES
1-alkynyl-1H-indole-2-carbaldehydes
domino addition/annulation
sodium
INTRAMOLECULAR CYCLIZATION
HETEROCYCLES
BETA-(2-AMINOPHENYL)-ALPHA,BETA-YNONES
CYCLIC ALKENYL ETHERS
CHEMISTRY
ORGANOPALLADIUM COMPLEXES
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Summary:The unusual [1,4]oxazino[4,3- a]indole nucleus was prepared, under mild reaction conditions, by reacting 1-alkynyl-1 H-indole-2-carbaldehydes with various alkoxides, generated in situ from the corresponding alkyl, benzyl, allyl and propargyl alcohols.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.08.102