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Kotte, Shylaja
- Synthesis of Piperidine Bound 3,4,5-Trisubstituted Isoxazolines Via 1,3- Dipolar Cycloaddition Reactions Catalyzed By N-Heterocyclic Carbene
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Authors
Prasad Gundepaka
1,
Shravankumar Kankala
2,
Hanmanthu Guguloth
2,
Shylaja Kotte
2,
Vinutha Chakilam
2,
Mukkanti Kagga
1,
Ravinder Vadde
2,
Chandra Sekhar Vasam
3
Affiliations
1 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
2 Department of Chemistry, Kakatiya University, Warangal, 506 009, IN
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001, IN
1 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
2 Department of Chemistry, Kakatiya University, Warangal, 506 009, IN
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001, IN
Source
Asian Journal of Research in Chemistry, Vol 6, No 10 (2013), Pagination: 916-919Abstract
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
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