Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner

Jinho Kim, S. Yunmi Lee, Junseung Lee, Youngkyu Do, Sukbok Chang

Research output: Contribution to journalArticle

94 Citations (Scopus)

Abstract

(Chemical Equation Presented) Ammonium salts were found to be a convenient and inexpensive reagent in the Cu-catalyzed three-component reaction with terminal alkynes and sulfonyl or phosphoryl azides leading to N-unprotected amidines. Thus obtained amidines bearing 2-bromobenzenesulfonyl moiety were efficiently cyclized by the Cu-catalyzed intramolecular N-arylation to give an important pharmacophore skeleton of 2H-1,2,4-benzothiadiazine 1,1-dioxides. Conveniently, two tandem catalytic procedures could be readily operated in one pot.

Original languageEnglish
Pages (from-to)9454-9457
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number23
DOIs
Publication statusPublished - 2008 Dec 5

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Amidines
Ammonium Compounds
Bearings (structural)
Salts
Alkynes
Azides
2H-1,2,4-benzothiadiazine-1,1-dioxide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Kim, Jinho ; Lee, S. Yunmi ; Lee, Junseung ; Do, Youngkyu ; Chang, Sukbok. / Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 23. pp. 9454-9457.
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Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner. / Kim, Jinho; Lee, S. Yunmi; Lee, Junseung; Do, Youngkyu; Chang, Sukbok.

In: Journal of Organic Chemistry, Vol. 73, No. 23, 05.12.2008, p. 9454-9457.

Research output: Contribution to journalArticle

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