Literature DB >> 20706616

Two step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines.

Zhigang Xu1, Justin Dietrich, Arthur Y Shaw, Christopher Hulme.   

Abstract

A two-step solution phase synthesis employing a double UDC (Ugi/Deprotect/Cyclize) strategy has been utilized to obtain fused 6,7,6,6-quinoxalinone-benzodiazepines and 6,7,7,6-bis-benzodiazepines. Optimization of the methodology to produce these tetracyclic scaffolds was enabled by microwave irradiation, incorporation of trifluoroethanol as solvent, and the use of the convertible isocyanide, 4-tert-butyl cyclohexen-1-yl isocyanide.

Entities:  

Year:  2010        PMID： 20706616      PMCID： PMC2917818          DOI： 10.1016/j.tetlet.2010.06.116

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  13 in total

1.  Maximizing synthetic efficiency: multi-component transformations lead the way

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Journal:  Chemistry       Date:  2000-09-15       Impact factor: 5.236

2.  Multicomponent Reactions with Isocyanides.

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Journal:  Angew Chem Int Ed Engl       Date:  2000-09-15       Impact factor: 15.336

Review 3.  "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

4.  Spirodiketopiperazine-based CCR5 antagonists: Lead optimization from biologically active metabolite.

Authors:  Rena Nishizawa; Toshihiko Nishiyama; Katsuya Hisaichi; Naoki Matsunaga; Chiaki Minamoto; Hiromu Habashita; Yoshikazu Takaoka; Masaaki Toda; Shiro Shibayama; Hideaki Tada; Kenji Sagawa; Daikichi Fukushima; Kenji Maeda; Hiroaki Mitsuya
Journal:  Bioorg Med Chem Lett       Date:  2006-11-01       Impact factor: 2.823

5.  Synthesis of Passerini-Ugi hybrids by a four-component reaction using the glycolaldehyde dimer.

Authors:  Riccardo Mossetti; Tracey Pirali; Gian Cesare Tron
Journal:  J Org Chem       Date:  2009-07-03       Impact factor: 4.354

Review 6.  Emerging approaches for the syntheses of bicyclic imidazo[1,2-x]-heterocycles.

Authors:  Christopher Hulme; Yeon-Sun Lee
Journal:  Mol Divers       Date:  2008-04-12       Impact factor: 2.943

Review 7.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2008.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Allan J Goodman; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2009 Sep-Oct

8.  The use of the Ugi four-component condensation.

Authors:  Stefano Marcaccini; Tomás Torroba
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

Review 9.  Rapid assembly of molecular diversity via exploitation of isocyanide-based multi-component reactions.

Authors:  Christopher Hulme; Thomas Nixey
Journal:  Curr Opin Drug Discov Devel       Date:  2003-11

10.  Synthesis of substituted imidazoles via organocatalysis.

Authors:  Doug E Frantz; Louis Morency; Arash Soheili; Jerry A Murry; Edward J J Grabowski; Richard D Tillyer
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  6 in total

1.  Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes.

Authors:  Zhigang Xu; Arthur Y Shaw; Gary S Nichol; Alexandra P Cappelli; Christopher Hulme
Journal:  Mol Divers       Date:  2012-05-24       Impact factor: 2.943

2.  A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations.

Authors:  Muhammad Ayaz; Justin Dietrich; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2011-09-21       Impact factor: 2.415

3.  Straightforward assembly of phenylimidazoquinoxalines via a one-pot two-step MCR process.

Authors:  Fabio De Moliner; Christopher Hulme
Journal:  Org Lett       Date:  2012-02-22       Impact factor: 6.005

4.  Synthesis of Constrained Heterocycles Employing Two Post-Ugi Cyclization Methods for Rapid Library Generation with In Cellulo Activity.

Authors:  Nicholas McConnell; Zhigang Xu; Vishnu Kumarasamy; Daekyu Sun; Brendan Frett; Hong-Yu Li
Journal:  ChemistrySelect       Date:  2017-12-19       Impact factor: 2.109

5.  Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation.

Authors:  Steven Gunawan; Muhammad Ayaz; Fabio De Moliner; Brendan Frett; Christine Kaiser; Nina Patrick; Zhigang Xu; Christopher Hulme
Journal:  Tetrahedron       Date:  2012-04-26       Impact factor: 2.457

6.  Recent Advances in the Development of Catalytic Methods that Construct Medium-ring Lactams, Partially Saturated Benzazepines and their Derivatives.

Authors:  Wrickban Mazumdar; Tom G Driver
Journal:  Synthesis (Stuttg)       Date:  2021       Impact factor: 3.157
  6 in total

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