Literature DB >> 16268559

Exploiting the dual reactivity of o-isocyanobenzamide: three-component synthesis of 4-imino-4H-3,1-benzoxazines.

Damien Bonne1, Mouloud Dekhane, Jieping Zhu.   

Abstract

[reaction: see text] A multicomponent synthesis of 4-imino-4H-3,1-benzoxazines is developed. Heating a toluene solution of an aldehyde (6), an amine (7), and an isonitrile (5) in the presence of a stoichiometric amount of ammonium chloride at 60 degrees C for 12 h produces the title compound in good to excellent yields.

Entities:  

Year:  2005        PMID: 16268559     DOI: 10.1021/ol052239w

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Ammonium chloride-catalyzed green multicomponent synthesis of dihydropyrazine and tetrahydrodiazepine derivatives "on water".

Authors:  Ahmad Shaabani; Heshmatollah Sepahvand; Shima Ghasemi
Journal:  Mol Divers       Date:  2018-11-21       Impact factor: 2.943

2.  DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate.

Authors:  Hui Chen; Peng Li; Rongfei Qin; Hong Yan; Gang Li; Haihong Huang
Journal:  ACS Omega       Date:  2020-04-16

3.  Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping.

Authors:  András Váradi; Travis C Palmer; Paula R Notis; Gabriel N Redel-Traub; Daniel Afonin; Joan J Subrath; Gavril W Pasternak; Chunhua Hu; Indrajeet Sharma; Susruta Majumdar
Journal:  Org Lett       Date:  2014-02-28       Impact factor: 6.005

Review 4.  Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles.

Authors:  András Váradi; Travis C Palmer; Rebecca Notis Dardashti; Susruta Majumdar
Journal:  Molecules       Date:  2015-12-23       Impact factor: 4.411

5.  Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway.

Authors:  Serge Zaretsky; Jennifer L Hickey; Joanne Tan; Dmitry Pichugin; Megan A St Denis; Spencer Ler; Benjamin K W Chung; Conor C G Scully; Andrei K Yudin
Journal:  Chem Sci       Date:  2015-07-07       Impact factor: 9.825

  5 in total

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