The Davis-Beirut reaction: N 1, N 2-disubstituted-1 H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2 H-indazoles

Wayne E. Conrad, Ryo Fukazawa, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A variety of electrophiles (anhydrides, acid chlorides, carbonochloridates, sulfonyl chlorides, and alkyl bromides) react with 3-methoxy-2H-indazole (1a), benzoxazin[3,2-b]indazole (1d), and oxazolino[3,2-b]indazole (1e) - substrates available by the Davis-Beirut reaction - to yield a diverse set of N 1,N2-disubstituted-1H-indazolones. With certain electrophiles, an AERORC (Addition of the Electrophile, Ring Opening, and Ring Closure) process on indazole 1d results in indazoloindazolone formation. An intriguing aspect of these N1,N2-disubstituted-1H- indazolones is that they are poised for diversification through, for example, azide-alkyne cycloaddition chemistry reported here.

Original languageEnglish (US)
Pages (from-to)3138-3141
Number of pages4
JournalOrganic Letters
Volume13
Issue number12
DOIs
StatePublished - Jun 17 2011

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Indazoles
chlorides
rings
cycloaddition
alkynes
anhydrides
closures
bromides
chemistry
acids
Alkynes
Azides
Cycloaddition
Anhydrides
Cycloaddition Reaction
Bromides
Chlorides
Acids
alkoxyl radical
Substrates

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

The Davis-Beirut reaction : N 1, N 2-disubstituted-1 H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2 H-indazoles. / Conrad, Wayne E.; Fukazawa, Ryo; Haddadin, Makhluf J.; Kurth, Mark J.

In: Organic Letters, Vol. 13, No. 12, 17.06.2011, p. 3138-3141.

Research output: Contribution to journalArticle

Conrad, Wayne E. ; Fukazawa, Ryo ; Haddadin, Makhluf J. ; Kurth, Mark J. / The Davis-Beirut reaction : N 1, N 2-disubstituted-1 H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2 H-indazoles. In: Organic Letters. 2011 ; Vol. 13, No. 12. pp. 3138-3141.
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