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Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

✍ Scribed by John M Gardiner; Jonathan Procter

Book ID
104230997
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
76 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

N-Alkoxy-, N-aryloxy-and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol for diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents.

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Synthesis of novel 2,2- and 1,1-linked d
Synthesis of novel 2,2- and 1,1-linked dimeric β€˜head-to-head’ N-alkoxybenzimidazoles
✍ John M. Gardiner; Andrew D. Goss; Tahir N. Majid; Andrew D. Morley πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 105 KB

Synthesis of two new types of 'head-to-head' N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeri