Literature DB >> 22920993

Synthesis of imidazopyridines from the Morita-Baylis-Hillman acetates of nitroalkenes and convenient access to Alpidem and Zolpidem.

Divya K Nair1, Shaikh M Mobin, Irishi N N Namboothiri.   

Abstract

A variety of functionalized imidazo[1,2-a]pyridines have been synthesized through a one-pot, room temperature, and reagent-free reaction between MBH acetates of nitroalkenes and 2-aminopyridines. The reaction involves a cascade inter-intramolecular double aza-Michael addition of 2-aminopyridines to MBH acetates. Our methodology is marked by excellent yield, regioselectivity and, above all, adaptability to synthesize imidazopyridine-based drug molecules such as Alpidem and Zolpidem.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22920993     DOI: 10.1021/ol3020418

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  14 in total

Review 1.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

2.  Selective, C-3 Friedel-Crafts acylation to generate functionally diverse, acetylated Imidazo[1,2-a]pyridine derivatives.

Authors:  Brendan Frett; Nicholas McConnell; Anupreet Kharbanda; Gunaganti Naresh; Benjamin Rounseville; Christina Warner; John Chang; Natalie Debolske; Hong-Yu Li
Journal:  Tetrahedron       Date:  2018-07-17       Impact factor: 2.457

3.  BF3-etherate promoted facile access to vinyloxyimidazopyridines: a metal-free sustainable approach.

Authors:  Saurabh Kumar Tiwari; Mohd Nazeef; Ankit Verma; Ankit Kumar; Vikas Yadav; Neetu Yadav; Saif Ansari; I R Siddiqui
Journal:  Mol Divers       Date:  2021-05-16       Impact factor: 2.943

Review 4.  An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883

5.  Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Authors:  Tao Shu; Qijian Ni; Xiaoxiao Song; Kun Zhao; Tianyu Wu; Rakesh Puttreddy; Kari Rissanen; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2016-01-11       Impact factor: 6.222

6.  Study on a Three-Step Rapid Assembly of Zolpidem and Its Fluorinated Analogues Employing Microwave-Assisted Chemistry.

Authors:  Nikola Fajkis; Monika Marcinkowska; Beata Gryzło; Anna Krupa; Marcin Kolaczkowski
Journal:  Molecules       Date:  2020-07-10       Impact factor: 4.411

7.  Efficient and "Green" Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)-Ascorbate-Catalyzed A3-Coupling in Aqueous Micellar Media.

Authors:  Zigmee T Bhutia; Dharmendra Das; Amrita Chatterjee; Mainak Banerjee
Journal:  ACS Omega       Date:  2019-03-01

8.  Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromo-phen-yl)imidazo[1,2-a]pyridine.

Authors:  Hussien Ahmed Khamees; Kumara Chaluvaiah; Nasseem Ahmed El-Khatatneh; Ananda Swamynayaka; Kwong Huey Chong; Jagadeesh Prasad Dasappa; Mahendra Madegowda
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-10-03

9.  Iodine Promoted Efficient Synthesis of 2-Arylimidazo[1,2-a]pyridines in Aqueous Media: A Comparative Study between Micellar Catalysis and an "On-Water" Platform.

Authors:  Zigmee T Bhutia; Padmini C Panjikar; Shruti Iyer; Amrita Chatterjee; Mainak Banerjee
Journal:  ACS Omega       Date:  2020-05-26

10.  Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation.

Authors:  Huey Chong Kwong; C S Chidan Kumar; Siau Hui Mah; Yew Leng Mah; Tze Shyang Chia; Ching Kheng Quah; Gin Keat Lim; Siddegowda Chandraju
Journal:  Sci Rep       Date:  2019-01-30       Impact factor: 4.379

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.