Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o‑Nitrosoimine Intermediate

Reaction options, alkoxide vs hydroxide vs amine addition to the key intermediate (o-nitrosoimine) generated in the Davis–Beirut reaction of an o-nitrobenzylamine substrate, are reported to explain the nucleophilic addition selectivity of this one-pot indazole-forming process. The hydroxide addition...

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Bibliographic Details
Published in:Organic letters 2018-03, Vol.20 (5), p.1308-1311
Main Authors: Zhu, Jie S, Duong, Matthew R, Teuthorn, Andrew P, Lu, Julia Y, Son, Jung-Ho, Haddadin, Makhluf J, Kurth, Mark J
Format: Article
Language:English
Subjects:
Amines
Hydroxides - chemistry
Imines
Indazoles
Molecular Structure
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Summary:Reaction options, alkoxide vs hydroxide vs amine addition to the key intermediate (o-nitrosoimine) generated in the Davis–Beirut reaction of an o-nitrobenzylamine substrate, are reported to explain the nucleophilic addition selectivity of this one-pot indazole-forming process. The hydroxide addition/deprotection pathway as well as the fate of the resulting o-nitrosobenzaldehyde were both uncovered with several o-nitrobenzylamine substrates, and design elements required for an efficient double Davis–Beirut reaction, inspired by new mechanistic insights, were defined.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00036