Building libraries of skeletally diverse scaffolds from novel heterocyclic active methylene compound through multi-component reactions

被引:12
作者
Jayarajan, Ramasamy [1 ]
Vasuki, Gnanasambandam [1 ]
机构
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
关键词
Novel heterocyclic active methylene compound; Diversity oriented synthesis; Multi-component reaction; Polycyclic heterocycles; Spiro heterocyclic scaffold; ONE-POT SYNTHESIS; ORIENTED SYNTHESIS; SPIROOXINDOLE DERIVATIVES; EFFICIENT SYNTHESIS; WATER; NAPHTHOPYRAN; STRATEGY;
D O I
10.1016/j.tetlet.2012.04.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Libraries of skeletally diverse potential bioactive polycyclic/spirocyclic heterocyclic compounds: 2-amino-7, 9-dimethyl-5-oxo-4-aryl-4,5,6,7-tetrahydropyrano[2,3-d]pyrazolo[3,4-b]pyridine-3-carbonitrile, 2'-amino-7',9'-dimethyl-2,5'-dioxo-6',7'-dihydro-5'H-spirorindoline-3,4'-pyrano[2,3-d]pyrazolo[3,4-blpyridine]-3'-carbonitrile, and 5,5'-(arylmethylene)bis(4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one) have been synthesized through a multi-component reaction using novel heterocyclic active methylene compound 4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-6(7H)-one as one of the building blocks. This protocol can be considered to be an efficient and eco-friendly strategy for diversity oriented synthesis. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3044 / 3048
页数:5
相关论文
共 41 条
[1]   Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]   An efficient green chemical approach for the synthesis of structurally diverse spiroheterocycles with fused heterosystems [J].
Arya, Anand Kumar ;
Kumar, Mahendra .
GREEN CHEMISTRY, 2011, 13 (05) :1332-1338
[3]   A planning strategy for diversity-oriented synthesis [J].
Burke, MD ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58
[4]   Efficient One-Pot Synthesis of Novell Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium [J].
Chen, Hui ;
Shi, Daqing .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04) :571-576
[5]  
Chiu G., 2006, PCT Int. Appl., Patent No. [2006130673, WO 2006130673]
[6]   An efficient synthesis of fluorine-containing substituted spiro[piperidine-4, 4′-pyrano[3,2-c]quinoline]-3′-carbonitrille by nonconventional methods [J].
Dandia, Anshu ;
Gautam, Sangeeta ;
Jain, Anuj Kumar .
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (12) :1454-1460
[7]   NMR kinetic investigations of the photochemical and thermal reactions of a photochromic chromene [J].
Delbaere, S ;
Micheau, JC ;
Vermeersch, G .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8968-8973
[8]   New MCR-Heck-isomerization cascade toward indoles [J].
El Kaim, Laurent ;
Gizzi, Marion ;
Grimaud, Laurence .
ORGANIC LETTERS, 2008, 10 (16) :3417-3419
[9]  
Feurer A., 2004, PCT Int. Aool. Wo, Patent No. 2004009589
[10]   Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].
Galliford, Chris V. ;
Scheidt, Karl A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758