SELECTIVE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS THROUGH THE INTRAMOLECULAR SUBSTITUTION OF PHENYLSELENONYL GROUP BY NITROGEN OR CARBONYL OXYGEN IN AMIDES

Nitrogen heterocycles were produced by the oxidation of N-[omega-(phenylseleno)alkyl]-p-toluenesulfonamides through the intramolecular substitution of the resultant phenylselenonyl group by the nitrogen atom. By the oxidation of the corresponding benzamides, on the other hand, cyclization by nitroge...

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Bibliographic Details
Published inTetrahedron letters Vol. 33; no. 28; pp. 4017 - 4020
Main Authors TOSHIMITSU, A, HIROSAWA, C, TANIMOTO, S, UEMURA, S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 07.07.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
VINYL SELENONES
SE
SELENONE
ALKOXIDES
SELENOXIDES
NITROGEN HETEROCYCLE
C-O BONDS
OXAZOLINE
ALKYL PHENYL SELENONES
DIHYDROOXAZINE
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Summary:Nitrogen heterocycles were produced by the oxidation of N-[omega-(phenylseleno)alkyl]-p-toluenesulfonamides through the intramolecular substitution of the resultant phenylselenonyl group by the nitrogen atom. By the oxidation of the corresponding benzamides, on the other hand, cyclization by nitrogen or carbonyl oxygen proceeded depending on the number of carbon atoms between the nucleophile (amide) and the leaving group (selenonyl group).
ISSN:0040-4039
DOI:10.1016/0040-4039(92)88089-N