A New Strategy in the Synthesis of Amide‐bearing Pyrrolizine from 2‐Pyroglutamic acid

Author:

Siddaraj Ranjith1,Ningegowda Raghu2,Swamy Shivananju Nanjunda3,Chandrashekharappa Sandeep4ORCID,Priya Babu S1

Affiliation:

1. Dept. of Studies in Chemistry University of Mysore, Manasa Gangotri Mysuru Karnataka India- 570006

2. Jyoti Nivas College Autonomous Department of Chemistry Bangalore 560095 India

3. Department of Biotechnology JSS Science and Technology University Mysuru 570006 India

4. Department of Medicinal Chemistry National Institute of Pharmaceutical Education and Research (NIPER−R) Raebareli Transit Campus Lucknow UP 226002 India

Abstract

AbstractThe present synthetic methodology is related to the synthesis of novel azabicycloalkanes and their synthetic analogues. New and convenient synthetic routes were developed for access to the novel Pyrrolizine, and its analogue was synthesized using a multi‐step synthesis methodology. A novel efficient synthesis of the azabicyclic ring system via Michael addition followed by the intramolecular ring closing method of pyrrolizine has been developed utilizing deprotection of the CBz group by hydrogenation followed by in‐situ Michael addition and intramolecular cyclization reaction as the key step. This methodology can be further taken forward to the pharmaceutically active natural products containing azabicyclic ring systems. All the synthesized compounds were characterized by spectroscopic methods like IH‐NMR, 13C‐NMR, LC‐MS, IR, and elemental analysis.

Publisher

Wiley

Subject

General Chemistry

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