Literature DB >> 29058229

Synthesis of functionalized dispiro[indoline-3,1[Formula: see text]-cyclopentane-3[Formula: see text],3[Formula: see text]-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoylhydrazides and arylhydrazines.

Ren-Yin Yang1, Jing Sun2, Gong Jin1, Chao-Guo Yan3.   

Abstract

The triethylamine-promoted domino cyclodimerization reaction of 3-phenacylideneoxindolines with benzohydrazides in acetonitrile afforded densely substituted dispiro[indoline-3,1[Formula: see text]-cyclopentane-3[Formula: see text],3[Formula: see text]-indolines] in good yields and with high diastereoselectivity. The similar domino reaction of 3-phenacylideneoxindoles with arylhydrazines also gave corresponding dispiro[indoline-3,1[Formula: see text]-cyclopentane-3[Formula: see text],3[Formula: see text]-indolines] with hydrazinyl or arylazo groups according to the structures of arylhydrazines.

Entities:  

Keywords:  Arylhydrazine; Benzoylhydrazide; Cyclodimerization; Dispiro[indoline-31-cyclopentane-33-indolines]; Spirooxindoline

Mesh：

Substances：

Year:  2017        PMID： 29058229     DOI： 10.1007/s11030-017-9786-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  28 in total

1.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Asymmetric synthesis of 3,3'-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence.

Authors:  Kun Zhao; Ying Zhi; Xinyi Li; Rakesh Puttreddy; Kari Rissanen; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2016-02-07       Impact factor: 6.222

3.  Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents.

Authors:  Chourouk Mhiri; Sarra Boudriga; Moheddine Askri; Michael Knorr; Dharmarajan Sriram; Perumal Yogeeswari; Frédéric Nana; Christopher Golz; Carsten Strohmann
Journal:  Bioorg Med Chem Lett       Date:  2015-07-26       Impact factor: 2.823

4.  Regioselectivity-Tunable Self-1,3-Dipolar [3+3] Cyclizations of Azomethine Ylides To Assemble Dispirooxindole-piperazines.

Authors:  Peng-Ju Xia; Yan-Hua Sun; Jun-An Xiao; Zhao-Fang Zhou; Sai-Shuai Wen; Yu Xiong; Guang-Chuan Ou; Xiao-Qing Chen; Hua Yang
Journal:  J Org Chem       Date:  2015-11-09       Impact factor: 4.354

5.  Diastereospecific and Enantioselective Access to Dispirooxindoles from Furfurylcyclobutanols by Means of a Pd-Catalyzed Arylative Dearomatization/Ring Expansion Cascade.

Authors:  Jianchao Liu; Hui Peng; Lin Lu; Xiaobing Xu; Huanfeng Jiang; Biaolin Yin
Journal:  Org Lett       Date:  2016-12-05       Impact factor: 6.005

6.  Construction of dispirocyclopentanebisoxindoles via self-domino Michael-aldol reactions of 3-phenacylideneoxindoles.

Authors:  Jing Sun; Ya-Jing Xie; Chao-Guo Yan
Journal:  J Org Chem       Date:  2013-08-26       Impact factor: 4.354

7.  Structural study of the solid-state photoaddition reaction of arylidenoxindoles

Authors: 
Journal:  J Org Chem       Date:  2000-06-02       Impact factor: 4.354

Review 8.  Spirooxindoles: Promising scaffolds for anticancer agents.

Authors:  Bin Yu; De-Quan Yu; Hong-Min Liu
Journal:  Eur J Med Chem       Date:  2014-06-27       Impact factor: 6.514

9.  Synthesis of Bis-pyrrolizidine-Fused Dispiro-oxindole Analogues of Curcumin via One-Pot Azomethine Ylide Cycloaddition: Experimental and Computational Approach toward Regio- and Diastereoselection.

Authors:  Yogesh P Bharitkar; Mohua Das; Neha Kumari; M Padma Kumari; Abhijit Hazra; Sagar S Bhayye; Ramalingam Natarajan; Siddharth Shah; Sourav Chatterjee; Nirup B Mondal
Journal:  Org Lett       Date:  2015-09-02       Impact factor: 6.005

Review 10.  Strategies for the enantioselective synthesis of spirooxindoles.

Authors:  Nicolas R Ball-Jones; Joseph J Badillo; Annaliese K Franz
Journal:  Org Biomol Chem       Date:  2012-05-14       Impact factor: 3.876
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  1 in total

1.  Tosylhydrazine-promoted self-conjugate reduction-Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives.

Authors:  Sayan Pramanik; Chhanda Mukhopadhyay
Journal:  Beilstein J Org Chem       Date:  2022-04-27       Impact factor: 2.544
  1 in total

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