Literature DB >> 23050691

Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles.

Jing Sun1, Yan Sun, Hui Gong, Ya-Jing Xie, Chao-Guo Yan.   

Abstract

A facile synthetic protocol was developed for the efficient synthesis of complex dispirooxindole-fused heterocycles via a three-component reaction. The key strategies involve a domino 1,4-dipolar addition and Diels-Alder reaction of the in situ generated Huisgen 1,4-dipoles from the addition reaction of 4-dimethylaminopyridine with acetylenedicarboxylate to 3-phenacylideneoxindole.

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Year:  2012        PMID： 23050691     DOI： 10.1021/ol302530m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Dipolar cycloaddition strategy for three-component synthesis of chromeno[3',4':3,4]pyrido[2,1-a]isoquinoline derivatives.

Authors:  Abdolali Alizadeh; Parinaz Jamal; Atefeh Roosta; Reza Rezaiyehraad; Tian-Fu Liu; Mojtaba Khanpour
Journal:  Mol Divers       Date:  2020-02-01       Impact factor: 2.943

2.  Synthesis of benzimidazole[2.1-b][1,3]oxazine spirooxindoles via three-component reaction of N-benzylbenzimidazole, acetylenedicarboxylates, and N-alkylisatins.

Authors:  Li-Juan Zhang; Chao-Guo Yan
Journal:  Mol Divers       Date:  2014-08-19       Impact factor: 2.943

3.  Molecular diversity of acid-catalyzed one-pot reaction of arylamines, methyl propiolate, and isatins.

Authors:  Hong Gao; Jing Sun; Chao-Guo Yan
Journal:  Mol Divers       Date:  2014-03-25       Impact factor: 2.943

4.  Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate.

Authors:  Hong Gao; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2013-12-27       Impact factor: 2.883

5.  Four-component bicyclization approaches to skeletally diverse pyrazolo[3,4-b]pyridine derivatives.

Authors:  Xing-Jun Tu; Wen-Juan Hao; Qin Ye; Shuang-Shuang Wang; Bo Jiang; Guigen Li; Shu-Jiang Tu
Journal:  J Org Chem       Date:  2014-11-04       Impact factor: 4.354

6.  Green synthesis of new pyrrolidine-fused spirooxindoles via three-component domino reaction in EtOH/H2O.

Authors:  Yong-Chao Wang; Jun-Liang Wang; Kevin S Burgess; Jiang-Wei Zhang; Qiu-Mei Zheng; Ya-Dan Pu; Li-Jun Yan; Xue-Bing Chen
Journal:  RSC Adv       Date:  2018-02-02       Impact factor: 4.036

7.  Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.

Authors:  Li-Juan Zhang; Qun Wu; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2013-05-02       Impact factor: 2.883

8.  Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction.

Authors:  Qin Fu; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2013-05-13       Impact factor: 2.883

9.  Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

Authors:  Jing Sun; Hui Gong; Yan Sun; Chao-Guo Yan
Journal:  Mol Divers       Date:  2013-07-19       Impact factor: 2.943

10.  Regioselectivity and diastereoselectivity of three-component reaction of α-amino acid, dialkyl acetylenedicarboxylates and 2-arylidene-1,3-indanediones.

Authors:  Liang Chen; Jing Sun; Ying Huang; Yu Zhang; Chao-Guo Yan
Journal:  Sci Rep       Date:  2017-09-29       Impact factor: 4.379
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