Literature DB >> 26470864

Synthesis of tricyclic quinazolinones via intramolecular cyclization of 3-(2-aminoalkyl)-2-(phenylamino)quinazolin-4(3H)-ones.

Xuhong Yang1, Minghu Wu1, Shaofa Sun1, Changfeng Huang2, Haibing Guo1, Jian Wang1, John Lee3, Yalan Xing4.   

Abstract

Bioactive tricyclic quinazolines class of 3,4-dihydro-1H-pyrimido[2,1-b]quinazolin-6(2H)-ones I and 2,3-dihydroimidazo[2,1-b]quinazolin-5(1H)-ones II were synthesized by the formic acid-catalyzed intramolecular cyclization of 3-(2-aminoalkyl)-2-(phenylamino)quinazolin-4(3H)-ones 1 in high yields. A plausible mechanism of the cyclization step is proposed.

Entities:  

Keywords:  Guanidines; Intramolecular cyclization; Tricyclic quinazoline

Mesh：

Substances：

Year:  2015        PMID： 26470864     DOI： 10.1007/s11030-015-9636-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  10 in total

1.  Enantioselective total synthesis of batzelladine F: structural revision and stereochemical definition.

Authors:  F Cohen; L E Overman
Journal:  J Am Chem Soc       Date:  2001-10-31       Impact factor: 15.419

2.  Synthesis, in vitro antiproliferative activity and DNA-interaction of benzimidazoquinazoline derivatives as potential anti-tumor agents.

Authors:  L Dalla Via; O Gia; S M Magno; A Da Settimo; A M Marini; G Primofiore; F Da Settimo; S Salerno
Journal:  Farmaco       Date:  2001-03

3.  Synthesis of 2,4-diaminoquinazolines and tricyclic quinazolines by cascade reductive cyclization of methyl N-cyano-2-nitrobenzimidates.

Authors:  Ping Yin; Nan Liu; Yu-Xing Deng; Yue Chen; Yong Deng; Ling He
Journal:  J Org Chem       Date:  2012-02-24       Impact factor: 4.354

4.  Application of neutral amidines and guanidines in coordination chemistry.

Authors:  Martyn P Coles
Journal:  Dalton Trans       Date:  2006-01-11       Impact factor: 4.390

Review 5.  The chemistry and biology of organic guanidine derivatives.

Authors:  Roberto G S Berlinck; Antonio Carlos B Burtoloso; Miriam H Kossuga
Journal:  Nat Prod Rep       Date:  2008-07-01       Impact factor: 13.423

6.  Enantioselective protonation catalyzed by a chiral bicyclic guanidine derivative.

Authors:  Dasheng Leow; Shishi Lin; Santhosh Kumar Chittimalla; Xiao Fu; Choon-Hong Tan
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Amidines. 2. A new class of antihypertensive agents. 1,2,3,5-Tetrahydroimidazo(2,1-b)quinazolines.

Authors:  T Jen; B Dienel; H Bowman; J Petta; A Helt; B Loev
Journal:  J Med Chem       Date:  1972-07       Impact factor: 7.446

8.  Benzimidazo[2,1-b]quinazolin-12-ones. A new class of potent immunosuppressive compounds.

Authors:  W H Lunn; R W Harper; R L Stone
Journal:  J Med Chem       Date:  1971-11       Impact factor: 7.446

9.  Radical synthesis of guanidines from N-acyl cyanamides.

Authors:  Marie-Hélène Larraufie; Cyril Ollivier; Louis Fensterbank; Max Malacria; Emmanuel Lacôte
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-15       Impact factor: 15.336

Review 10.  Molecular recognition of oxoanions based on guanidinium receptors.

Authors:  Pascal Blondeau; Margarita Segura; Ruth Pérez-Fernández; Javier de Mendoza
Journal:  Chem Soc Rev       Date:  2006-11-09       Impact factor: 54.564
  10 in total

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