Literature DB >> 22592603

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.

Hamid Mofakham1, Ahmad Shaabani, Sajjad Mousavifaraz, Fatemeh Hajishaabanha, Shabnam Shaabani, Seik Weng Ng.   

Abstract

A novel and efficient method has been developed for the one-pot synthesis of bifunctional diazepine-tetrazole containing compounds. 1H-Tetrazolyl-1H-1,4-diazepine-2, 3-dicarbonitrile and 1H-tetrazolyl-benzo[b][1,4]diazepine derivatives were synthesized in good yields using 2,3-diaminomaleonitrile or an aromatic diamine, ketones, trimethylsilyl azide, and an isocyanide in the presence of p-toluenesulfonic acid as a catalyst in methanol at room temperature.

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Year:  2012        PMID: 22592603     DOI: 10.1007/s11030-012-9371-4

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


  14 in total

Review 1.  "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.

Authors:  Christopher Hulme; Vijay Gore
Journal:  Curr Med Chem       Date:  2003-01       Impact factor: 4.530

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

Authors:  Ahmad Shaabani; Ali Maleki; Jafar Moghimi-Rad
Journal:  J Org Chem       Date:  2007-07-04       Impact factor: 4.354

3.  Novel 1,5-benzodiazepines as CCK-B ligands. Effect of aryl-carbamic substituents at the C-3 position together with halogen substitution on the benzo-fused ring.

Authors:  M E Tranquillini; P G Cassarà; M Corsi; G Curotto; D Donati; G Finizia; G Pentassuglia; S Polinelli; G Tarzia; A Ursini; F T van Amsterdam
Journal:  Arch Pharm (Weinheim)       Date:  1997-11       Impact factor: 3.751

4.  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

5.  Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists.

Authors:  B E Evans; K E Rittle; M G Bock; R M DiPardo; R M Freidinger; W L Whitter; G F Lundell; D F Veber; P S Anderson; R S Chang
Journal:  J Med Chem       Date:  1988-12       Impact factor: 7.446

6.  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

7.  Novel syntheses of tetrahydrobenzodiazepines and dihydropyrazines via isocyanide-based multicomponent reactions of diamines.

Authors:  Ahmad Shaabani; Ali Maleki; Fatemeh Hajishaabanha; Hamid Mofakham; Mozhdeh Seyyedhamzeh; Mojtaba Mahyari; Seik Weng Ng
Journal:  J Comb Chem       Date:  2010 Jan-Feb

8.  Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives.

Authors:  Ahmad Shaabani; Ali Maleki; Hamid Mofakham; Hamid Reza Khavasi
Journal:  J Comb Chem       Date:  2008-02-01

9.  Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines.

Authors:  Fredrik Ek; Sophie Manner; Lars-Göran Wistrand; Torbjörn Frejd
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354

10.  Novel multicomponent one-pot synthesis of tetrahydro-1H-1,5-benzodiazepine-2-carboxamide derivatives.

Authors:  Ahmad Shaabani; Ali Maleki; Hamid Mofakham
Journal:  J Comb Chem       Date:  2008-06-14
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  5 in total

Review 1.  Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

Authors:  Simpal Kumari; Dharma Kishore; Sarvesh Paliwal; Rajani Chauhan; Jaya Dwivedi; Aakanksha Mishra
Journal:  Mol Divers       Date:  2015-06-09       Impact factor: 2.943

Review 2.  The status of isocyanide-based multi-component reactions in Iran (2010-2018).

Authors:  Ronak Afshari; Seyyed Emad Hooshmand; Mohammad Taghi Nazeri; Siamak Javanbakht; Ahmad Shaabani; Reza Mohammadian
Journal:  Mol Divers       Date:  2020-02-18       Impact factor: 2.943

Review 3.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

4.  Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes.

Authors:  Alexander A Titov; Reza Samavati; Elena V Alexandrova; Tatiana N Borisova; Tuyet Anh Dang Thi; Van Tuyen Nguyen; Tuan Anh Le; Alexey V Varlamov; Erik V Van der Eycken; Leonid G Voskressensky
Journal:  Molecules       Date:  2018-11-17       Impact factor: 4.411

5.  Study of novel triazolo-benzodiazepine analogues as antidepressants targeting by molecular docking and ADMET properties prediction.

Authors:  Assia Belhassan; Hanane Zaki; Mohamed Benlyas; Tahar Lakhlifi; Mohammed Bouachrine
Journal:  Heliyon       Date:  2019-09-09
  5 in total

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