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Davis-Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate.
Zhu, Jie S; Duong, Matthew R; Teuthorn, Andrew P; Lu, Julia Y; Son, Jung-Ho; Haddadin, Makhluf J; Kurth, Mark J.
Affiliation
  • Zhu JS; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
  • Duong MR; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
  • Teuthorn AP; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
  • Lu JY; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
  • Son JH; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
  • Haddadin MJ; Department of Chemistry, American University of Beirut , Beirut 1107 2020, Lebanon.
  • Kurth MJ; Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
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.
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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
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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