α,β-Unsaturated diazoketones as useful platforms in the synthesis of nitrogen heterocycles

Accounts of Chemical Research
Antonio C B BurtolosoBarbara Bernardim

Abstract

Among the different types of diazocarbonyl substrates found in the literature to date, α,β-unsaturated diazoketones have proven to be very promising as multifunctional intermediates. Possessing a diazo group, a ketone function and a double bond all together in a single molecule, these compounds constitute versatile building blocks for synthesis. For example, double bond functionalization, followed by intramolecular insertion reactions, can be a short alternative to prepare several rings or heterocyclic compounds. Although there are many efficient methods to prepare diazoketones, very few can be extended to the synthesis of the a,β-unsaturated diazoketones; this is likely responsible for their limited application in synthesis. Unfortunately, the classical methods to prepare saturated- or aryl-diazoketones (acylation of diazomethane with acyl chlorides or mixed anhydrides) are not suitable for preparing a,β-unsaturated diazoketones, since pyrazolines (dipolar cycloaddition products from the reaction between diazomethane and the double bond) are formed. Although Danheiser's two-step detrifluoroacetylative procedure (starting from a,β-unsaturated methyl ketones) is considered the best general method, it cannot be applied to the syn...Continue Reading

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Citations

Nov 5, 2016·The Journal of Organic Chemistry·Meire Y KawamuraAntonio C B Burtoloso
Nov 23, 2016·Chemistry : a European Journal·Sam G MossJoseph B Sweeney
Dec 1, 2015·Chemical Communications : Chem Comm·Maciej GiedykDorota Gryko
Jul 21, 2017·Chemical Society Reviews·Qing-Qing ChengMichael P Doyle
Nov 22, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shicheng Shi, Michal Szostak
Jul 21, 2020·Expert Opinion on Therapeutic Patents·Kamal M Dawood, Ashraf A Abbas
Apr 19, 2018·Anais Da Academia Brasileira De Ciências·Antonio C B BurtolosoGraziele L Novais
Jan 27, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Daniel SoléIsrael Fernández
Feb 4, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·David P DayAntonio C B Burtoloso
Mar 17, 2021·The Journal of Organic Chemistry·Sigrid GavelleCatherine Gaulon-Nourry
Apr 29, 2021·Organic & Biomolecular Chemistry·Se Hyun KimJun Hee Lee
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anton BudeevMikhail Krasavin
Jun 25, 2021·Chemical Science·Pu ChenMichal Szostak
Oct 29, 2019·The Journal of Organic Chemistry·Jack Everson, Milton J Kiefel

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