Literature DB >> 30937596

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

Sedigheh Akrami1, Bahador Karami2, Mahnaz Farahi1.   

Abstract

Herein, an effectual, quick and novel method is described for the synthesis of new triazolo[1,5-a]pyrimidine, triazolo[5,1-b][1,3] thiazine and pyrazolo[1,5-a]pyrimidine derivatives. This series of fused six-member rings to triazole and pyrazole was prepared via the catalyst-free reaction of dialkyl acetylenedicarboxylates and 3-substituted 1H-1,2,4-triazole or 3-amino-1H-pyrazole-4-carbonitrile. The structures of the prepared products were deduced from their Fourier-transform infrared, elemental analysis and proton and carbon-13 nuclear magnetic resonance spectral data. A novel and green method is described for the synthesis of new triazolo[1,5-a]pyrimidine, triazolo[5,1-b][1,3] thiazine and pyrazolo[1,5-a]pyrimidine derivatives.

Entities:  

Keywords:  3-Amino-1H-1,2,4-triazole; 3-Amino-1H-pyrazole-4-carbonitrile; Dialkyl acetylenedicarboxylates; Pyrazolo[15-a]pyrimidine; Triazolo[1,5-a]pyrimidine; Triazolo[5,1-b][1,3] thiazine

Year:  2019        PMID: 30937596     DOI: 10.1007/s11030-019-09944-5

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


  19 in total

1.  Synthesis of pyrazolo[1,5-alpha]pyrimidinone regioisomers.

Authors:  Lori K Gavrin; Arthur Lee; Brian A Provencher; Walter W Massefski; Stephen D Huhn; Gregory M Ciszewski; Derek C Cole; John C McKew
Journal:  J Org Chem       Date:  2007-02-02       Impact factor: 4.354

2.  Synthesis and SAR of a new series of COX-2-selective inhibitors: pyrazolo[1,5-a]pyrimidines.

Authors:  C Almansa; A F de Arriba; F L Cavalcanti; L A Gómez; A Miralles; M Merlos; J García-Rafanell; J Forn
Journal:  J Med Chem       Date:  2001-02-01       Impact factor: 7.446

3.  Synthesis and evaluation of 1,2,4-triazolo[1,5-a]pyrimidines as antibacterial agents against Enterococcus faecium.

Authors:  Huan Wang; Mijoon Lee; Zhihong Peng; Blas Blázquez; Elena Lastochkin; Malika Kumarasiri; Renee Bouley; Mayland Chang; Shahriar Mobashery
Journal:  J Med Chem       Date:  2015-05-12       Impact factor: 7.446

4.  Liquid-phase synthesis of combinatorial libraries based on 7-trifluoromethyl-substituted pyrazolo[1,5-a]pyrimidine scaffold.

Authors:  Igor L Dalinger; Irina A Vatsadse; Svyatoslav A Shevelev; Alexandre V Ivachtchenko
Journal:  J Comb Chem       Date:  2005 Mar-Apr

5.  Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents.

Authors:  U Sankappa Rai; Arun M Isloor; Prakash shetty; A M Vijesh; Nithin Prabhu; Shrikrishna Isloor; M Thiageeswaran; Hoong-Kun Fun
Journal:  Eur J Med Chem       Date:  2010-02-20       Impact factor: 6.514

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

Authors:  Ahmad Shaabani; Mozhdeh Seyyedhamzeh; Nasim Ganji; Mona Hamidzad Sangachin; Mahsa Armaghan
Journal:  Mol Divers       Date:  2015-05-28       Impact factor: 2.943

7.  Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents.

Authors:  A H Abdel-Rahman; E M Keshk; M A Hanna; Sh M el-Bady
Journal:  Bioorg Med Chem       Date:  2004-05-01       Impact factor: 3.641

8.  Synthesis and chemical-pharmacological characterization of the antimetastatic NAMI-A-type Ru(III) complexes (Hdmtp)[trans-RuCl4(dmso-S)(dmtp)], (Na)[trans-RuCl4(dmso-S)(dmtp)], and [mer-RuCl3(H2O)(dmso-S)(dmtp)] (dmtp = 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine).

Authors:  Aldrik H Velders; Alberta Bergamo; Enzo Alessio; Ennio Zangrando; Jaap G Haasnoot; Claudia Casarsa; Moreno Cocchietto; Sonia Zorzet; Gianni Sava
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

9.  Synthesis and biological evaluations of pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 inhibitors.

Authors:  Dong Chan Kim; Yeo Ran Lee; Beom-Seok Yang; Kye Jung Shin; Dong Jin Kim; Bong Young Chung; Kyung Ho Yoo
Journal:  Eur J Med Chem       Date:  2003-05       Impact factor: 6.514

10.  Essramycin: a first triazolopyrimidine antibiotic isolated from nature.

Authors:  Mervat M A El-Gendy; Mohamed Shaaban; Khaled A Shaaban; Ahmed M El-Bondkly; Hartmut Laatsch
Journal:  J Antibiot (Tokyo)       Date:  2008-03       Impact factor: 2.649

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  1 in total

Review 1.  Functional Pyrazolo[1,5-a]pyrimidines: Current Approaches in Synthetic Transformations and Uses As an Antitumor Scaffold.

Authors:  Andres Arias-Gómez; Andrés Godoy; Jaime Portilla
Journal:  Molecules       Date:  2021-05-05       Impact factor: 4.411

  1 in total

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