Literature DB >> 17608537

A novel isocyanide-based three-component reaction: synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives.

Ahmad Shaabani1, Ali Maleki, Jafar Moghimi-Rad.   

Abstract

A novel multi-component synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives starting from simple and readily available inputs is described. Thus, simply stirring an ethanol solution of 2,3-diaminomaleonitrile, a ketone, and an isocyanide in the presence of a catalytic amount of p-toluenesulfonic acid provided highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives in good to excellent yields at ambient temperature.

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Year:  2007        PMID: 17608537     DOI: 10.1021/jo0707131

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

Review 1.  Recent progress of isocyanide-based multicomponent reactions in Iran.

Authors:  Ahmad Shaabani; Ali Maleki; Ali Hossein Rezayan; Afshin Sarvary
Journal:  Mol Divers       Date:  2010-07-29       Impact factor: 2.943

2.  A novel one-pot pseudo-five-component condensation reaction towards bifunctional diazepine-tetrazole containing compounds: synthesis of 1H-tetrazolyl-1H-1,4-diazepine-2,3-dicarbonitriles and 1H-tetrazolyl-benzo[b][1,4]diazepines.

Authors:  Hamid Mofakham; Ahmad Shaabani; Sajjad Mousavifaraz; Fatemeh Hajishaabanha; Shabnam Shaabani; Seik Weng Ng
Journal:  Mol Divers       Date:  2012-05-17       Impact factor: 2.943

3.  Synthesis of 2-(1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-ones from diaminoglyoxime-based nitrones.

Authors:  Rahim Hosseinzadeh-Khanmiri; Abolghasem Moghimi; Ahmad Shaabani; Hassan Valizadeh; Seik Weng Ng
Journal:  Mol Divers       Date:  2015-04-22       Impact factor: 2.943

4.  Ammonium chloride-catalyzed green multicomponent synthesis of dihydropyrazine and tetrahydrodiazepine derivatives "on water".

Authors:  Ahmad Shaabani; Heshmatollah Sepahvand; Shima Ghasemi
Journal:  Mol Divers       Date:  2018-11-21       Impact factor: 2.943

5.  Diaminoglyoxime as a versatile reagent in the synthesis of bis(1,2,4-oxadiazoles), 1,2,4-oxadiazolyl-quinazolines and 1,2,4-oxadiazolyl-benzothiazinones.

Authors:  Rahim Hosseinzadeh Khanmiri; Abolghasem Moghimi; Ahmad Shaabani; Hassan Valizadeh; Seik Weng Ng
Journal:  Mol Divers       Date:  2014-08-13       Impact factor: 2.943

6.  A new one-pot three-component synthesis of 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives.

Authors:  Ahmad Shaabani; Fatemeh Hajishaabanha; Hamid Mofakham; Ali Maleki
Journal:  Mol Divers       Date:  2009-05-16       Impact factor: 2.943

7.  A novel synthesis of highly substituted imidazo[1,5-a]pyrazine derivatives by 3-CR/2-CR sequence.

Authors:  Ahmad Shaabani; Ali Maleki; Hamid Mofakham
Journal:  Mol Divers       Date:  2008-11-21       Impact factor: 2.943

8.  A novel class of extended pi-conjugated systems: one-pot synthesis of bis-3-aminoimidazo[1,2-a]pyridines, pyrimidines and pyrazines.

Authors:  Ahmad Shaabani; Ebrahim Soleimani; Ali Maleki; Jafar Moghimi-Rad
Journal:  Mol Divers       Date:  2008-12-02       Impact factor: 3.364

9.  Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping.

Authors:  András Váradi; Travis C Palmer; Paula R Notis; Gabriel N Redel-Traub; Daniel Afonin; Joan J Subrath; Gavril W Pasternak; Chunhua Hu; Indrajeet Sharma; Susruta Majumdar
Journal:  Org Lett       Date:  2014-02-28       Impact factor: 6.005

10.  A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions.

Authors:  Shabnam Shaabani; Ahmad Shaabani; Monika Kucerakova; Michal Dusek
Journal:  Front Chem       Date:  2019-09-18       Impact factor: 5.221

  10 in total

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