Literature DB >> 19719182

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.

Ahmad Shaabani1, Ali Hossein Rezayan, Sajjad Keshipour, Afshin Sarvary, Seik Weng Ng.   

Abstract

A novel and efficient method has been developed for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives using an aromatic diamine, Meldrum's acid, and an isocyanide in CH(2)Cl(2) at ambient temperature in high yields without using any catalyst or activation. The procedure provides an alternative method for the synthesis of benzo[b][1,5]diazepine derivatives. These compounds have closely related ring systems such as triflubazam, clobazam, and 1,5-benzodiazepines, which have a broad spectrum of biological activities.

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Year:  2009        PMID: 19719182     DOI: 10.1021/ol901196z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  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.

Authors:  Ahmad Shaabani; Heshmatollah Sepahvand; Mahmoud Borjian Boroujeni; Mohammad Tayeb Faroghi
Journal:  Mol Divers       Date:  2017-01-12       Impact factor: 2.943

3.  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

4.  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

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.  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 Characterization of Biodegradable Semi-Interpenetrating Polymer Networks Based on Star-Shaped Copolymers of ɛ-Caprolactone and Lactide.

Authors:  Ali Hossein Rezayan; Negar Firoozi; Somayyeh Kheirjou; Seyed Jamal Tabatabaei Rezaei; Mohammad Reza Nabid
Journal:  Iran J Pharm Res       Date:  2017       Impact factor: 1.696

8.  Synthesis and Biological Evaluation of Thiosemicarbazide Derivatives Endowed with High Activity toward Mycobacterium Bovis.

Authors:  Soroush Sardari; Samaneh Feizi; Ali Hossein Rezayan; Parisa Azerang; Seyyed Mohammad Shahcheragh; Ghazaleh Ghavami; Azizollah Habibi
Journal:  Iran J Pharm Res       Date:  2017       Impact factor: 1.696

9.  Synthesis of Novel Fluorene Bisamide Derivatives via Ugi Reaction and Evaluation their Biological Activity against Mycobacterium species.

Authors:  Ali Hossein Rezayan; Safoura Hariri; Parisa Azerang; Ghazaleh Ghavami; Isabel Portugal; Soroush Sardari
Journal:  Iran J Pharm Res       Date:  2017       Impact factor: 1.696

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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