Literature DB >> 21838278

Concise palladium-catalyzed synthesis of dibenzodiazepines and structural analogues.

Dmitry Tsvelikhovsky1, Stephen L Buchwald.   

Abstract

A general and highly efficient protocol for the synthesis of dibenzodiazepines and their structural analogues is reported. In the presence of catalytic quantities of palladium, readily accessible precursors are cross-coupled with ammonia and then spontaneously undergo an intramolecular condensation to form the corresponding dibenzodiazepines in one step. This new strategy is applicable to the construction of a wide variety of dibenzooxazepines and other structurally related heterocycles.

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Year:  2011        PMID: 21838278      PMCID: PMC3175814          DOI: 10.1021/ja206229y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  30 in total

1.  Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines.

Authors:  David S Surry; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-08-02       Impact factor: 15.419

2.  Method development for a pyridobenzodiazepine library with multiple diversification points.

Authors:  Fuqiang Shi; Xianxiu Xu; Lianyou Zheng; Qun Dang; Xu Bai
Journal:  J Comb Chem       Date:  2008-02-09

3.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

4.  Pharmacological properties of Sintamil, a new antidepressant agent.

Authors:  J David; R S Grewal
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5.  Synthesis of novel tricyclic pyrimido[4,5-b][1,4]benzothiazepines via Bischler-Napieralski-type reactions.

Authors:  Renzhong Fu; Xianxiu Xu; Qun Dang; Xu Bai
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

6.  New (sulfonyloxy)piperazinyldibenzazepines as potential atypical antipsychotics: chemistry and pharmacological evaluation.

Authors:  Y Liao; B J Venhuis; N Rodenhuis; W Timmerman; H Wikström; E Meier; G D Bartoszyk; H Böttcher; C A Seyfried; S Sundell
Journal:  J Med Chem       Date:  1999-06-17       Impact factor: 7.446

Review 7.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Diazepinomicin, a new antimicrobial alkaloid from a marine Micromonospora sp.

Authors:  Romila D Charan; Gerhard Schlingmann; Jeffrey Janso; Valerie Bernan; Xidong Feng; Guy T Carter
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

9.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

10.  Evaluating indole-related derivatives as precursors in the directed biosynthesis of diazepinomicin analogues.

Authors:  Anokha S Ratnayake; Jeffrey E Janso; Xidong Feng; Gerhard Schlingmann; Igor Goljer; Guy T Carter
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

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  3 in total

Review 1.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

2.  Double heteroatom functionalization of arenes using benzyne three-component coupling.

Authors:  José-Antonio García-López; Meliha Çetin; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

3.  Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group.

Authors:  Tej Narayan Poudel; Yong Rok Lee
Journal:  Chem Sci       Date:  2015-09-16       Impact factor: 9.825

  3 in total

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