Regioselective annulation of nitrosopyridine with alkynes: straightforward synthesis of N-oxide-imidazopyridines

Chemical Communications : Chem Comm
Srimanta MannaAndrey P Antonchick

Abstract

We have developed a novel method for the regioselective annulation of 2-nitrosopyridines with variably substituted alkynes under mild reaction conditions. This approach allows the annulation of alkynes with 2-nitrosopyridines under reagent- and catalyst-free reaction conditions. The developed method shows excellent functional group tolerance and provides easy access to N-oxide-imidazo[1,2-a]pyridines.

References

Dec 4, 1998·Journal of Medicinal Chemistry·A GueiffierJ P Chapat
Apr 1, 2004·Journal of the American Chemical Society·Yuhei Yamamoto, Hisashi Yamamoto
Jul 13, 2005·Chemical Communications : Chem Comm·Hisashi Yamamoto, Norie Momiyama
Oct 15, 2005·Angewandte Chemie·Yuhei Yamamoto, Hisashi Yamamoto
Nov 23, 2005·Proceedings of the National Academy of Sciences of the United States of America·Marcus A KochHerbert Waldmann
May 20, 2006·Nature Chemical Biology·Ryan Hili, Andrei K Yudin
Sep 28, 2007·Mini Reviews in Medicinal Chemistry·Cécile Enguehard-Gueiffier, Alain Gueiffier
Apr 15, 2008·Molecular Diversity·Christopher Hulme, Yeon-Sun Lee
Dec 20, 2008·Journal of the American Chemical Society·Andrea PenoniKenneth M Nicholas
Apr 8, 2009·Journal of Medicinal Chemistry·William R PittColin R Groom
Jan 30, 2010·Chemical Society Reviews·Benito AlcaideCristina Aragoncillo
Apr 27, 2010·Chemical Society Reviews·Prasad AppukkuttanErik V Van der Eycken
Mar 25, 2011·Chemical Society Reviews·Gema Domínguez, Javier Pérez-Castells
Apr 27, 2011·Angewandte Chemie·Brian S Bodnar, Marvin J Miller
May 28, 2011·Chemical Reviews·Albert Moyano, Ramon Rios
Sep 29, 2012·Chemical Communications : Chem Comm·Chuan HeAiwen Lei
Nov 17, 2012·Chemical Reviews·Kai E O Ylijoki, Jeffrey M Stryker
Nov 23, 2012·Chemical Society Reviews·Géraldine MassonGuillaume Dagousset
Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan
Jan 12, 2013·Angewandte Chemie·Kiran Matcha, Andrey P Antonchick
Feb 1, 2013·Angewandte Chemie·Shyamal ChakrabartyArmido Studer
Feb 1, 2013·Angewandte Chemie·Andrey P Antonchick, Lars Burgmann
Jan 30, 2014·Journal of Medicinal Chemistry·Richard D TaylorAlastair D G Lawson
Mar 8, 2014·Chemistry : a European Journal·Rishikesh Narayan, Andrey P Antonchick
Mar 20, 2014·Chemical Society Reviews·Fernando López, José L Mascareñas
Apr 16, 2014·Accounts of Chemical Research·Rishikesh NarayanHerbert Waldmann
May 20, 2014·Advanced Synthesis & Catalysis·Eric P A TalbotF Dean Toste
May 23, 2014·Angewandte Chemie·Srimanta Manna, Andrey P Antonchick

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Citations

Sep 4, 2015·Organic Letters·Srimanta MannaOleg N Chupakhin
Aug 27, 2015·Organic Letters·Praveen Reddy AdiyalaRam Awatar Maurya
Aug 19, 2015·Organic Letters·Srimanta Manna, Andrey P Antonchick
Jun 13, 2015·Organic Letters·Luis Bering, Andrey P Antonchick
Oct 7, 2016·Chemical Communications : Chem Comm·Roberta CaporasoAndrey P Antonchick
Mar 21, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Chitrakar Ravi, Subbarayappa Adimurthy
Jun 1, 2017·Chemistry : a European Journal·Luis BeringAndrey P Antonchick
Feb 18, 2020·Chemical Communications : Chem Comm·Subhra Kanti RoyChandan K Jana
Nov 15, 2020·Chemical Communications : Chem Comm·Anisha PurkaitChandan K Jana

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