Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

Wei Jan Huang, Om V. Singh, Chung Hsiung Chen, Sheng You Chiou, Shoei Sheng Lee

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3,4-dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the oxidation of other isoquinolines, including tetrahydroisoquinolines, lycorine diacetate, and benzyltetrahydroisoquinolines, also afforded the corresponding lactams in good yields, however, accompanied by a few minor byproducts. Under similar conditions, tetrahydroberberine gave a rearranged compound, berberal, as the major product, accompanied by 8-oxoberberine and berberine.

Original languageEnglish
Pages (from-to)1069-1078
Number of pages10
JournalHelvetica Chimica Acta
Volume85
Issue number4
DOIs
Publication statusPublished - 2002
Externally publishedYes

Fingerprint

Isoquinolines
Tetrahydroisoquinolines
Berberine
Lactams
Alkaloids
alkaloids
iodides
Chemical activation
activation
Oxidation
oxidation
Byproducts
products
8-oxoberberine
lycorine
isoquinoline
tetrabutylammonium
canadine
iodosobenzene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids. / Huang, Wei Jan; Singh, Om V.; Chen, Chung Hsiung; Chiou, Sheng You; Lee, Shoei Sheng.

In: Helvetica Chimica Acta, Vol. 85, No. 4, 2002, p. 1069-1078.

Research output: Contribution to journalArticle

Huang, Wei Jan ; Singh, Om V. ; Chen, Chung Hsiung ; Chiou, Sheng You ; Lee, Shoei Sheng. / Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids. In: Helvetica Chimica Acta. 2002 ; Vol. 85, No. 4. pp. 1069-1078.
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