Literature DB >> 22330239

Concise one-pot preparation of unique bis-pyrrolidinone tetrazoles.

Steven Gunawan, Joachim Petit, Christopher Hulme.   

Abstract

A one-pot, two-step synthesis of bis-pyrrolidinone tetrazoles has been established via the Ugi-Azide reaction using methyl levulinate, primary amines, isocyanides and azidotrimethylsilane with subsequent acid treatment to catalyze the lactam formation. The efficiency of the protocol was established followed by a successful transition to library production in four 24-well plates.

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Year:  2012        PMID: 22330239      PMCID: PMC3299871          DOI: 10.1021/co200209a

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN: 2156-8944            Impact factor:   3.784


  6 in total

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3.  Concise approach toward tetrazolo[1,5-a][1,4]benzodiazepines via a novel multicomponent isocyanide-based condensation.

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Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

Review 4.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

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

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Review 6.  5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods.

Authors:  R Jason Herr
Journal:  Bioorg Med Chem       Date:  2002-11       Impact factor: 3.641

  6 in total
  15 in total

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

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Review 3.  Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

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Journal:  Mol Divers       Date:  2015-06-09       Impact factor: 2.943

4.  MCR synthesis of a tetracyclic tetrazole scaffold.

Authors:  Pravin Patil; Kareem Khoury; Eberhardt Herdtweck; Alexander Dömling
Journal:  Bioorg Med Chem       Date:  2014-12-20       Impact factor: 3.641

5.  Diastereoselective One Pot Five-Component Reaction toward 4-(Tetrazole)-1,3-Oxazinanes.

Authors:  Ajay L Chandgude; Daniele Narducci; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal:  RSC Adv       Date:  2017-10-26       Impact factor: 3.361

Review 6.  Tetrazoles via Multicomponent Reactions.

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

7.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

8.  Ugi 4-CR Synthesis of γ- and δ-Lactams providing new access to diverse enzyme interactions, a PDB analysis.

Authors:  André Boltjes; George P Liao; Ting Zhao; Eberhardt Herdtweck; Alexander Dömling
Journal:  Medchemcomm       Date:  2014-07-01       Impact factor: 3.597

9.  Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity.

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Journal:  Org Biomol Chem       Date:  2013-09-28       Impact factor: 3.876

10.  A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families.

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