Literature DB >> 28670172

New Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines.

Wen-Juan Hao1, Peng Zhou1, Fei-Yue Wu1, Bo Jiang1,2, Shu-Jiang Tu1, Guigen Li2,3.   

Abstract

A novel three-component bicyclization for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines has been established from readily accessible aryl aldehydes, α-thiocyanate ketones and pyrazol-5-amines. The reaction pathway involves nucleophilic addition/5-exo-trig /6-endo-trig bicyclization sequence, resulting in continuous multiple bond-forming events including C-N and C-C bonds to rapidly a molecular complexity.

Entities:  

Keywords:  Bicyclization; Microwave Heating; Multicomponent Reactions; Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines; α-thiocyanate ketones

Year:  2016        PMID： 28670172      PMCID： PMC5489242          DOI： 10.1002/ejoc.201600163

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  34 in total

1.  Four-component domino reaction leading to multifunctionalized quinazolines.

Authors:  Bo Jiang; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

2.  An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones.

Authors:  Feng-Cheng Jia; Cheng Xu; Qun Cai; An-Xin Wu
Journal:  Chem Commun (Camb)       Date:  2014-09-07       Impact factor: 6.222

3.  One-pot five-component synthesis of spirocyclopenta[b]chromene derivatives and their acid-catalyzed rearrangement.

Authors:  Michael A Terzidis; Tryfon Zarganes-Tzitzikas; Constantinos Tsimenidis; Julia Stephanidou-Stephanatou; Constantinos A Tsoleridis; George E Kostakis
Journal:  J Org Chem       Date:  2012-09-28       Impact factor: 4.354

4.  Indium(III) Chloride-Catalyzed Isocyanide Insertion Reaction to Construct Complex Spirooxindole.

Authors:  Yaming Tian; Lumin Tian; Xiang He; Chunju Li; Xueshun Jia; Jian Li
Journal:  Org Lett       Date:  2015-09-11       Impact factor: 6.005

5.  Catalytic Ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine: access to asymmetric construction of several heterocycles.

Authors:  Liang Xia; Sheng Li; Ruijiao Chen; Kai Liu; Xiaochuan Chen
Journal:  J Org Chem       Date:  2013-03-06       Impact factor: 4.354

6.  Ritanserin, a 5-HT2 receptor antagonist, increases subcortical blood flow following photothrombotic middle cerebral artery occlusion in rats.

Authors:  T Back; R Prado; W Zhao; B D Watson; M D Ginsberg
Journal:  Neurol Res       Date:  1998-10       Impact factor: 2.448

7.  Isocyanide-based multicomponent reactions: catalyst-free stereoselective construction of polycyclic spiroindolines.

Authors:  Xiang Wang; Shun-Yi Wang; Shun-Jun Ji
Journal:  Org Lett       Date:  2013-04-08       Impact factor: 6.005

8.  The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.

Authors:  Lutz F Tietze; Tom Kinzel; C Christian Brazel
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

9.  Domino reaction of arylglyoxals with pyrazol-5-amines: selective access to pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles.

Authors:  Bo Jiang; Wei Fan; Mu-Yan Sun; Qin Ye; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  J Org Chem       Date:  2014-05-22       Impact factor: 4.354

10.  Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates.

Authors:  Zhen-Zhen Chen; Shuai Liu; Wen-Juan Hao; Ge Xu; Shuo Wu; Jiao-Na Miao; Bo Jiang; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  Chem Sci       Date:  2015-11-13       Impact factor: 9.825
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