Davis-Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate.
Org Lett
; 20(5): 1308-1311, 2018 03 02.
Article
in En
| MEDLINE
| ID: mdl-29431446
ABSTRACT
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Hydroxides
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2018
Document type:
Article
Affiliation country:
United States