Literature DB >> 26016722

One-pot four-component synthesis of highly substituted [1,2,4]triazolo[1,5-a]pyrimidines.

Ahmad Shaabani1, Mozhdeh Seyyedhamzeh2, Nasim Ganji2, Mona Hamidzad Sangachin2, Mahsa Armaghan3.   

Abstract

A green one-pot four-component strategy has been developed for the synthesis of [1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives using an amine, 2,2,6-trimethyl-4H-1,3-dioxin-4-one, an aldehyde, and 3-amino-1,2,4-triazole in the presence of a catalytic amount of p-toluenesulfonic acid in water within 4-6 h.

Entities:  

Keywords:  Green chemistry; MCRs; Multicomponent reaction; Triazolopyrimidine; Water

Mesh:

Substances:

Year:  2015        PMID: 26016722     DOI: 10.1007/s11030-015-9604-4

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


  15 in total

1.  Green chemistry oriented organic synthesis in water.

Authors:  Marc-Olivier Simon; Chao-Jun Li
Journal:  Chem Soc Rev       Date:  2011-11-02       Impact factor: 54.564

2.  Synthesis and biological study of 3-(phenylsulfonyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines as potent and selective serotonin 5-HT6 receptor antagonists.

Authors:  Alexandre V Ivachtchenko; Elena S Golovina; Madina G Kadieva; Angela G Koryakova; Sergiy M Kovalenko; Oleg D Mitkin; Ilya M Okun; Irina M Ravnyeyko; Sergey E Tkachenko; Oleg V Zaremba
Journal:  Bioorg Med Chem       Date:  2010-05-24       Impact factor: 3.641

3.  Synthesis and SAR of [1,2,4]triazolo[1,5-a]pyrimidines, a class of anticancer agents with a unique mechanism of tubulin inhibition.

Authors:  Nan Zhang; Semiramis Ayral-Kaloustian; Thai Nguyen; Jay Afragola; Richard Hernandez; Judy Lucas; James Gibbons; Carl Beyer
Journal:  J Med Chem       Date:  2007-01-25       Impact factor: 7.446

4.  New one-pot four-component synthesis of disubstituted pyrido[2,3-d]pyrimidine-6-carboxamide derivatives.

Authors:  Ahmad Shaabani; Mozhdeh Seyyedhamzeh; Ali Maleki; Fahimeh Rezazadeh; Maryam Behnam
Journal:  J Comb Chem       Date:  2009 May-Jun

5.  Studies on cardiovascular agents. 6. Synthesis and coronary vasodilating and antihypertensive activities of 1,2,4-triazolo[1,5-a]pyrimidines fused to heterocyclic systems.

Authors:  Y Sato; Y Shimoji; H Fujita; H Nishino; H Mizuno; S Kobayashi; S Kumakura
Journal:  J Med Chem       Date:  1980-08       Impact factor: 7.446

6.  Fluorinated 1,2,4-Triazolo[1,5-a]pyrimidine-6-carboxylic acid derivatives as antimycobacterial agents.

Authors:  Hamdy M Abdel-Rahman; Nawal A El-Koussi; Hoda Y Hassan
Journal:  Arch Pharm (Weinheim)       Date:  2009-02       Impact factor: 3.751

7.  One-pot synthesis of coumarin-3-carboxamides containing a triazole ring via an isocyanide-based six-component reaction.

Authors:  Shabnam Shaabani; Ahmad Shaabani; Seik Weng Ng
Journal:  ACS Comb Sci       Date:  2014-02-24       Impact factor: 3.784

8.  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

9.  Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives.

Authors:  Qiong Chen; Xiao-Lei Zhu; Li-Li Jiang; Zu-Ming Liu; Guang-Fu Yang
Journal:  Eur J Med Chem       Date:  2007-05-27       Impact factor: 6.514

10.  2-(Alkylthio)-1,2,4-triazolo[1,5-a]pyrimidines as adenosine cyclic 3',5'-monophosphate phosphodiesterase inhibitors with potential as new cardiovascular agents.

Authors:  T Novinson; R H Springer; D E O'Brien; M B Scholten; J P Miller; R K Robins
Journal:  J Med Chem       Date:  1982-04       Impact factor: 7.446

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  3 in total

1.  A novel protocol for catalyst-free synthesis of fused six-member rings to triazole and pyrazole.

Authors:  Sedigheh Akrami; Bahador Karami; Mahnaz Farahi
Journal:  Mol Divers       Date:  2019-04-01       Impact factor: 2.943

Review 2.  α-Aminoazoles/azines: key reaction partners for multicomponent reactions.

Authors:  Shah Imtiaz; Jahangir Ahmad War; Syqa Banoo; Sarfaraz Khan
Journal:  RSC Adv       Date:  2021-03-16       Impact factor: 3.361

Review 3.  Strategies for synthesis of 1,2,4-triazole-containing scaffolds using 3-amino-1,2,4-triazole.

Authors:  Shima Nasri; Mohammad Bayat; Khudaidad Kochia
Journal:  Mol Divers       Date:  2021-02-19       Impact factor: 2.943

  3 in total

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