Literature DB >> 22237832

Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines.

Zhigang Xu1, Arthur Y Shaw, Justin Dietrich, Alexandra P Cappelli, Gary Nichol, Christopher Hulme.   

Abstract

Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22237832      PMCID： PMC3311162          DOI： 10.1007/s11030-011-9354-x

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


  15 in total

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

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

2.  Multicomponent Reactions with Isocyanides.

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

3.  Multicomponent reactions are accelerated in water.

Authors:  Michael C Pirrung; Koushik Das Sarma
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419

Review 4.  "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

Review 5.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

6.  The discovery of GSK221149A: a potent and selective oxytocin antagonist.

Authors:  John Liddle; Michael J Allen; Alan D Borthwick; David P Brooks; David E Davies; Richard M Edwards; Anne M Exall; Chris Hamlett; Wendy R Irving; Andrew M Mason; Gerald P McCafferty; Fabrizio Nerozzi; Simon Peace; Joanne Philp; Derek Pollard; Mark A Pullen; Shaila S Shabbir; Steve L Sollis; Timothy D Westfall; Pat M Woollard; Charlene Wu; Deirdre M B Hickey
Journal:  Bioorg Med Chem Lett       Date:  2007-11-06       Impact factor: 2.823

Review 7.  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 8.  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

9.  Multicomponent synthesis of fused benzimidazolopiperazines.

Authors:  Laurent El Kaïm; Laurence Grimaud; Srinivas Reddy Purumandla
Journal:  J Org Chem       Date:  2011-05-10       Impact factor: 4.354

10.  One-step assembly of carbamoyl-substituted heteroannelated [1,4]thiazepines.

Authors:  Alexey P Ilyn; Marina V Loseva; Vladimir Y Vvedensky; Elena B Putsykina; Sergey E Tkachenko; Dmitri V Kravchenko; Alexandr V Khvat; Mikhail Y Krasavin; Alexandre V Ivachtchenko
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354
View more
  7 in total

1.  Facile microwave-assisted synthesis of benzimidazole scaffolds via Ugi-type three-component condensation (3CC) reactions.

Authors:  Gui-Ting Song; Zhi-Gang Xu; Dian-Yong Tang; Shi-Qiang Li; Zhi-Gang Xie; Hong-Liang Zhong; Zhi-Wei Yang; Jin Zhu; Jin Zhang; Zhong-Zhu Chen
Journal:  Mol Divers       Date:  2015-11-18       Impact factor: 2.943

2.  Exploiting the Divalent Nature of Isonitriles: a novel Pictet-Spengler Amidination process.

Authors:  Federico Medda; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2014-05-01       Impact factor: 2.415

3.  Synthesis of isoindolin-1-one derivatives via multicomponent reactions of methyl 2-formylbenzoate and intramolecular amidation.

Authors:  Jie Lei; Zhi-Gang Xu; Shi-Qiang Li; Jia Xu; Jin Zhu; Zhong-Zhu Chen
Journal:  Mol Divers       Date:  2016-06-07       Impact factor: 2.943

4.  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

5.  General one-pot, two-step protocol accessing a range of novel polycyclic heterocycles with high skeletal diversity.

Authors:  Zhigang Xu; Muhammad Ayaz; Alexandra A Cappelli; Christopher Hulme
Journal:  ACS Comb Sci       Date:  2012-07-12       Impact factor: 3.784

6.  K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- and light-free conditions.

Authors:  Nibedita Baruah Dutta; Mayurakhi Bhuyan; Gakul Baishya
Journal:  RSC Adv       Date:  2020-01-22       Impact factor: 4.036

7.  Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors:  Amarendar Reddy Maddirala; Peter R Andreana
Journal:  Beilstein J Org Chem       Date:  2018-04-18       Impact factor: 2.883
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.