Journal :   Asian Journal of Research in Chemistry

Volume No. :   6

Issue No. :  10

Year :  2013

Pages :   916-919

ISSN Print :  0974-4169

ISSN Online :  0974-4150


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Synthesis of Piperidine Bound 3,4,5-Trisubstituted Isoxazolines Via 1,3- Dipolar Cycloaddition Reactions Catalyzed By N-Heterocyclic Carbene



Address:   Prasad Gundepaka1,3, Shravankumar Kankala2*, Hanmanthu Guguloth2, Shylaja Kotte2, Vinutha Chakilam2, Mukkanti Kagga1, Ravinder Vadde2*, Chandra Sekhar Vasam3*
1Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad, India.
2Department of Chemistry, Kakatiya University, Warangal, India -506 009,
3Department of Chemistry, Satavahana University, Karimnagar, India-505 001,
*Corresponding Author
DOI No:

ABSTRACT:
A first example of organo-N-heterocyclic carbene (NHC) catalyzed click-type fast 1,3-dipolar cycloaddition of nitrile oxides with piperidine alkene alkaloids was developed for the regioselective synthesis of 3,4,5-trisubstituted isoxazolines. Triethylamine (Et3N) was employed as an effective base to generate both nitrile oxide and the organo-NHC catalyst in situ. This catalytic approach was used to attach a variety of substituents, including other biologically active fragments, onto the isoxazoline ring to selectively design multinucleus structures. A catalytic cycle is proposed and the remarkable regiocontrol in the formation of isoxazolines was ascribed to a beneficial zwitterion intermediate developed by the interaction of the strongly nucleophilic organo-NHC catalyst with alkene followed by nitrile oxide.
KEYWORDS:
1,3-Dipolar Cycloaddition, N-heterocyclic Carbene, Isoxazolines, piperidine alkene alkaloids.
Cite:
Prasad Gundepaka, Shravankumar Kankala, Hanmanthu Guguloth, Shylaja Kotte, Vinutha Chakilam, Mukkanti Kagga, Ravinder Vadde, Chandra Sekhar Vasam. Synthesis of Piperidine Bound 3,4,5-Trisubstituted Isoxazolines Via 1,3- Dipolar Cycloaddition Reactions Catalyzed By N-Heterocyclic Carbene. Asian J. Research Chem. 6(10): October 2013; Page 916-919.
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