Ethyl 3-halo-3-nitroacrylates: synthesis and reactions with primary aromatic amines

Kuritsyna, M. A.; Pelipko, V. V.; Kataeva, О. N.; Байчурин, Р. И.; Sadikov, K. D.; Smirnov, A. S.; Makarenko, S. V.

doi:10.1007/s11172-021-3257-5

Cited by 11 publications

(1 citation statement)

References 37 publications

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“…[80] Incorporation of the halogen into the β-position of initial β-nitroenoate changed the reaction pathway. [81,82] As expected, in the first step β-halo-β-nitroarcylates 79 added secondary aliphatic or primary aromatic amines to give the aza-Michael adduct 80. In the case of anilines these α-amino-β-nitro esters 80 were isolated in 88-95% yields.…”

Section: Conjugate Nucleophilic Addition To β-Nitroenoatesmentioning

confidence: 58%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

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Aza‐Michael addition is known to be one of the most exploited reactions in organic chemistry. Taking into account the fact that each seventh reaction in pharmaceutical industry involves the formation of at least one C−N bond, it is not surprising that this reaction is especially valuable for the synthesis of bioactive compounds and drugs. Traditionally, only push‐pull alkenes are regarded as starting material for this reaction. The participation of pull‐pull alkenes as Michael acceptors is much less studied. The presence of two vicinal electron‐withdrawing groups makes them highly reactive in nucleophilic reactions especially with nitrogen‐centered nucleophiles. This feature allows them to be excellent building blocks in the synthesis of bioactive molecules and polyfunctional materials. The review considers the most important and sometimes unexpected results obtained over the last two decades on the conjugate addition of nitrogen nucleophiles to pull‐pull alkenes bearing various acceptor moieties (alkoxycarbonyl‐, carbonyl‐, formyl‐, cyano‐, trifluoromethyl‐ or nitro group) in various combinations.

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Section: Conjugate Nucleophilic Addition To β-Nitroenoatesmentioning

confidence: 58%