Issue 11, 2024
From the journal:

Organic Chemistry Frontiers

A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines†

Sachin Sharma,a   Ajit Kumar Jhaa  and  Srinivasan Easwar ORCID logo *a  

* Corresponding authors

a Department of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, NH-8, Bandarsindri Dist., Ajmer, Rajasthan 305817, India
E-mail: easwar.srinivasan@curaj.ac.in
Tel: +91-1463-257508

Abstract

Explicit evidence of a retro-Mannich reaction triggered by a vicinal diamine upon its interaction with Morita–Baylis–Hillman ketones was gained by the use of a substrate derived from cyclohex-2-en-1-one. The reaction of such cyclic MBH ketones with ethylene diamine resulted in the formation of novel 5-alkylidene octahydroimidazo[1,2-a]pyridines; a range of substrates, which could also be generated in situ, participated in swift fashion to deliver good yields of the fused hetero-bicyclic products.

Graphical abstract: A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines

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Article information

DOI
https://doi.org/10.1039/D4QO00352G
Article type
Research Article
Submitted
23 Feb 2024
Accepted
08 Apr 2024
First published
09 Apr 2024

Org. Chem. Front., 2024,11, 3137-3150

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A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines

S. Sharma, A. K. Jha and S. Easwar, Org. Chem. Front., 2024, 11, 3137 DOI: 10.1039/D4QO00352G

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