Asian Journal of Research in Chemistry

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


Affiliations
1 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
2 Department of Chemistry, Kakatiya University, Warangal, 506 009, India
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001, India
     

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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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  • 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
Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
Shravankumar Kankala
Department of Chemistry, Kakatiya University, Warangal, 506 009, India
Hanmanthu Guguloth
Department of Chemistry, Kakatiya University, Warangal, 506 009, India
Shylaja Kotte
Department of Chemistry, Kakatiya University, Warangal, 506 009, India
Vinutha Chakilam
Department of Chemistry, Kakatiya University, Warangal, 506 009, India
Mukkanti Kagga
Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
Ravinder Vadde
Department of Chemistry, Kakatiya University, Warangal, 506 009, India
Chandra Sekhar Vasam
Department of Chemistry, Satavahana University, Karimnagar, 505 001, India

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

References