Literature DB >> 19132705

Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

James D Sunderhaus1, Stephen F Martin.   

Abstract

The sequencing of multicomponent reactions (MCRs) and subsequent cyclization reactions is a powerful stratagem for the rapid synthesis of diverse heterocyclic scaffolds. The optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products. The growing interest in diversity-oriented synthesis has led to increased attention to this paradigm for library synthesis, which has inspired many advances in the design and implementation of MCRs for the construction of diverse heterocyclic scaffolds.

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Year:  2009        PMID: 19132705      PMCID: PMC2803615          DOI: 10.1002/chem.200802140

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  25 in total

1.  Diversity-oriented synthesis; a challenge for synthetic chemists.

Authors:  David R Spring
Journal:  Org Biomol Chem       Date:  2003-11-21       Impact factor: 3.876

Review 2.  Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction.

Authors:  Paul A Tempest
Journal:  Curr Opin Drug Discov Devel       Date:  2005-11

3.  New Ugi-Smiles-metathesis strategy toward the synthesis of pyrimido azepines.

Authors:  Laurent El Kaïm; Laurence Grimaud; Julie Oble
Journal:  J Org Chem       Date:  2007-06-22       Impact factor: 4.354

4.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds.

Authors:  Eamon Comer; Erin Rohan; Li Deng; John A Porco
Journal:  Org Lett       Date:  2007-05-02       Impact factor: 6.005

Review 5.  Diversity-oriented synthesis; a spectrum of approaches and results.

Authors:  Richard J Spandl; Andreas Bender; David R Spring
Journal:  Org Biomol Chem       Date:  2008-02-19       Impact factor: 3.876

6.  The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates.

Authors:  B H Yang; S L Buchwald
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

7.  A new multicomponent coupling of aldehydes, amides, and dienophiles: atom-efficient one-pot synthesis of highly substituted cyclohexenes and cyclohexadienes.

Authors:  H Neumann; A J von Wangelin; D Gördes; A Spannenberg; M Beller
Journal:  J Am Chem Soc       Date:  2001-08-29       Impact factor: 15.419

8.  Synthesis of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by sequential Ugi/[2+2] ene-enone photocycloadditions.

Authors:  Irini Akritopoulou-Zanze; Alan Whitehead; Jan E Waters; Rodger F Henry; Stevan W Djuric
Journal:  Org Lett       Date:  2007-02-27       Impact factor: 6.005

9.  Generation of molecular diversity using a complexity-generating MCR-platform towards triazinane diones.

Authors:  Bas Groenendaal; Eelco Ruijter; Frans J J de Kanter; Martin Lutz; Anthony L Spek; Romano V A Orru
Journal:  Org Biomol Chem       Date:  2008-07-03       Impact factor: 3.876

10.  A multicomponent synthesis of triazinane diones.

Authors:  Bas Groenendaal; Danielle J Vugts; Rob F Schmitz; Frans J J de Kanter; Eelco Ruijter; Marinus B Groen; Romano V A Orru
Journal:  J Org Chem       Date:  2007-12-21       Impact factor: 4.354

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  67 in total

1.  REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.

Authors:  Jin-Peng Zhang; Wei Fan; Jie Ding; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Heterocycles       Date:  2013-12-17       Impact factor: 0.831

2.  Synthesis and diversification of 1,2,3-triazole-fused 1,4-benzodiazepine scaffolds.

Authors:  James R Donald; Stephen F Martin
Journal:  Org Lett       Date:  2011-01-28       Impact factor: 6.005

3.  Facile and unified approach to skeletally diverse, privileged scaffolds.

Authors:  James J Sahn; Justin Y Su; Stephen F Martin
Journal:  Org Lett       Date:  2011-04-22       Impact factor: 6.005

4.  Three-component reactions of isocyanides, dialkyl acetylenedicarboxylates, and trans-cinnamoyl chlorides for the synthesis of highly functionalized 2-vinyl furans.

Authors:  Abbas Ali Esmaeili; Mahdieh Zangouei; Rahele Hosseinabadi; Ali Reza Fakhari
Journal:  Mol Divers       Date:  2011-12-16       Impact factor: 2.943

5.  Novel and efficient one-pot five- and six-component reactions for the stereoselective synthesis of highly functionalized enaminones and dithiocarbamates.

Authors:  Morteza Bararjanian; Saeed Balalaie; Frank Rominger; Barahman Movassagh; Hamid Reza Bijanzadeh
Journal:  Mol Divers       Date:  2010-11-12       Impact factor: 2.943

6.  Multicomponent assembly strategies for the synthesis of diverse tetrahydroisoquinoline scaffolds.

Authors:  Brett A Granger; Kyosuke Kaneda; Stephen F Martin
Journal:  Org Lett       Date:  2011-08-11       Impact factor: 6.005

7.  Application of a sequential multicomponent assembly process/huisgen cycloaddition strategy to the preparation of libraries of 1,2,3-triazole-fused 1,4-benzodiazepines.

Authors:  James R Donald; Rebekah R Wood; Stephen F Martin
Journal:  ACS Comb Sci       Date:  2012-02-01       Impact factor: 3.784

8.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

9.  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.

Authors:  Simon Hardy; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-10-07       Impact factor: 2.457

10.  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

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