Literature DB >> 28083767

A green one-pot three-component cascade reaction: the synthesis of 2-amino-5,8-dihydro-3H-pyrido[2,3-D]pyrimidin-4-ones in aqueous medium.

Ahmad Shaabani1, Heshmatollah Sepahvand2, Mahmoud Borjian Boroujeni2, Mohammad Tayeb Faroghi2.   

Abstract

A one-pot three-component cascade reaction for the green synthesis of a new class of 2-amino-5,8-dihydro-3H-pyrido[2,3-d]pyrimidin-4-ones was developed from the condensation of aromatic aldehydes with 2,6-diaminopyrimidin-4(3H)-one and acetophenone derivatives or various cyclic ketones in the presence of a catalytic amount of sodium carbonate in a mixture of water and ethanol at 60  [Formula: see text]. This reaction led to the construction of two carbon-carbon bonds and one carbon-nitrogen bond in a single synthetic step.

Entities:  

Keywords:  2, 6-Diaminopyrimidin-4(3H)-one; Acetophenone; Dihydropyridopyrimidine; Green synthesis; MCR; Three-component reaction

Mesh：

Substances：

Year:  2017        PMID： 28083767     DOI： 10.1007/s11030-016-9712-9

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


  12 in total

1.  Biphenyl-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-methylamide (CA224), a nonplanar analogue of fascaplysin, inhibits Cdk4 and tubulin polymerization: evaluation of in vitro and in vivo anticancer activity.

Authors:  Sachin Mahale; Sandip B Bharate; Sudhakar Manda; Prashant Joshi; Sonali S Bharate; Paul R Jenkins; Ram A Vishwakarma; Bhabatosh Chaudhuri
Journal:  J Med Chem       Date:  2014-11-14       Impact factor: 7.446

2.  Novel N-linked aminopiperidine inhibitors of bacterial topoisomerase type II with reduced pK(a): antibacterial agents with an improved safety profile.

Authors:  Folkert Reck; Richard A Alm; Patrick Brassil; Joseph V Newman; Paul Ciaccio; John McNulty; Herbert Barthlow; Kosalaram Goteti; John Breen; Janelle Comita-Prevoir; Mark Cronin; David E Ehmann; Bolin Geng; Andrew Aydon Godfrey; Stewart L Fisher
Journal:  J Med Chem       Date:  2012-07-20       Impact factor: 7.446

3.  Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors.

Authors:  Diaa A Ibrahim; Nasser S M Ismail
Journal:  Eur J Med Chem       Date:  2011-10-01       Impact factor: 6.514

4.  New potential inhibitors of cyclin-dependent kinase 4: design and synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation.

Authors:  Shujiang Tu; Jinpeng Zhang; Xiaotong Zhu; Jianing Xu; Yan Zhang; Qian Wang; Runhong Jia; Bo Jiang; Junyong Zhang
Journal:  Bioorg Med Chem Lett       Date:  2006-04-18       Impact factor: 2.823

5.  Pyrido[2,3-d]pyrimidin-7-one inhibitors of cyclin-dependent kinases.

Authors:  M Barvian; D H Boschelli; J Cossrow; E Dobrusin; A Fattaey; A Fritsch; D Fry; P Harvey; P Keller; M Garrett; F La; W Leopold; D McNamara; M Quin; S Trumpp-Kallmeyer; P Toogood; Z Wu; E Zhang
Journal:  J Med Chem       Date:  2000-11-30       Impact factor: 7.446

6.  Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives.

Authors:  Ahmad Shaabani; Hamid Mofakham; Ali Maleki; Fatemeh Hajishaabanha
Journal:  J Comb Chem       Date:  2010-09-13

7.  Substrate-controlled chemoselective synthesis and potent cytotoxic activity of novel 5,6,7-triarylpyrido[2,3-d]pyrimidin-4-one derivatives.

Authors:  Feng Shi; Jie Ding; Shu Zhang; Wen-Juan Hao; Chuang Cheng; Shujiang Tu
Journal:  Bioorg Med Chem Lett       Date:  2010-09-29       Impact factor: 2.823

8.  Simple three-component method for the synthesis of spiroindeno[1,2-b]pyrido[2,3-d]pyrimidine-5,3'-indolines.

Authors:  Ghazaleh Imani Shakibaei; Afsaneh Feiz; Hamid Reza Khavasi; Ali Abolhasani Soorki; Ayoob Bazgir
Journal:  ACS Comb Sci       Date:  2010-11-09       Impact factor: 3.784

9.  A novel one-pot three-(in situ five-)component condensation reaction: an unexpected approach for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives.

Authors:  Ahmad Shaabani; Ali Hossein Rezayan; Sajjad Keshipour; Afshin Sarvary; Seik Weng Ng
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

10.  A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines.

Authors:  Mark C Bagley; James W Dale; Justin Bower
Journal:  Chem Commun (Camb)       Date:  2002-08-21       Impact factor: 6.222
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