Literature DB >> 17348669

A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives.

Paul Zhichkin1, Edward Kesicki, Jennifer Treiberg, Lisa Bourdon, Matthew Ronsheim, Hua Chee Ooi, Stephen White, Angela Judkins, David Fairfax.   

Abstract

[structure: see text]. An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee >93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

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Year:  2007        PMID: 17348669     DOI: 10.1021/ol070276c

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


  15 in total

1.  N-Butyl-4-chloro-benzamide.

Authors:  Aamer Saeed; Rasheed Ahmad Khera; Naeem Abbas; Jim Simpson; Roderick G Stanley
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-13

2.  N-Cyclo-hexyl-3,4,5-trimethoxy-benzamide.

Authors:  Aamer Saeed; Muhammad Arshad; Rasheed Ahmad Khera; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-28

3.  N-(2-Methoxy-phen-yl)-2-nitro-benzamide.

Authors:  Aamer Saeed; Shahid Hussain; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-20

4.  N-(4-Methoxy-phen-yl)pivalamide.

Authors:  Aamer Saeed; Shahid Hussain; Mahira Batool; Ulrich Flörke
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-08

5.  4-Chloro-N-(3-methoxy-phen-yl)-benz-amide.

Authors:  Aamer Saeed; Rasheed Ahmad Khera; Naeem Abbas; Jim Simpson; Roderick G Stanley
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-20

6.  4-Chloro-N-m-tolyl-benzamide.

Authors:  Aamer Saeed; Madiha Irfan; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-20

7.  N-(2-Methyl-phen-yl)-2-nitro-benzamide.

Authors:  Aamer Saeed; Shahid Hussain; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-01-25

8.  4-Chloro-N-cyclo-hexyl-benzamide.

Authors:  Aamer Saeed; Rasheed Ahmad Khera; Muhammad Latif; Masood Parvez
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-10

9.  2,4-Dichloro-N-cyclo-hexyl-benzamide.

Authors:  Aamer Saeed; Naeem Abbas; Shahid Hussain; Ulrich Flörke
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-02

10.  4-Chloro-N-(2-chloro-phen-yl)benzamide.

Authors:  Aamer Saeed; Rasheed Ahmad Khera; Kazuma Gotoh; Hiroyuki Ishida
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-13
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