94447-61-7Relevant academic research and scientific papers
An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles
Agafonova, Anastasiya V.,Funt, Liya D.,Novikov, Mikhail S.,Khlebnikov, Alexander F.
, p. 1976 - 1984 (2021/03/16)
A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(ii) catalysis. Alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylate formation are presented.
General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies
Fernandes, Alessandra A. G.,da Silva, Amanda F.,Okada, Celso Y.,Suzukawa, Vitor,Cormanich, Rodrigo A.,Jurberg, Igor D.
, p. 3022 - 3034 (2019/05/17)
A general platform for the conversion of isoxazol-5-ones to 3,5-disubstituted isoxazoles has been developed via a two-step strategy. The first step leads to the formation of 5-(pseudo)halogenated isoxazoles, while in the second, a variety of heteroalkyl-, heteroaryl-, alkyl-, alkenyl-, alkynyl- and aryl-chains can be installed via nucleophilic substitutions or palladium catalyzed cross-coupling reactions.
Easy Access to 2-Fluoro- And 2-Iodo-2 H -azirines via the Halex Reaction
Agafonova, Anastasiya V.,Khlebnikov, Alexander F.,Novikov, Mikhail S.,Rostovskii, Nikolai V.,Smetanin, Ilia A.
, p. 4582 - 4589 (2019/12/11)
A simple gram-scale method for the preparation of esters and dialkylamides of 2-(fluoro/iodo)-2 H -azirine-2-carboxylic acids via the halogen exchange (Halex) reaction of 2-bromo-substituted analogues is reported. The method operates with inexpensive and safe reagents, Bu 4 NF and potassium iodide, providing high product yields. Alternatively, 2-fluoro-2 H -azirine-2-carboxylates can be prepared from 2-iodo- and 2-chloro-analogues. The latter compounds can be obtained in practically quantitative yield by treating the 2-iodo- and 2-bromo-2 H -azirine-2-carboxylic esters with Bu 4 NCl.
Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines
Rostovskii, Nikolai V.,Agafonova, Anastasiya V.,Smetanin, Ilia A.,Novikov, Mikhail S.,Khlebnikov, Alexander F.,Ruvinskaya, Julia O.,Starova, Galina L.
, p. 4478 - 4488 (2017/09/26)
A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.
SYNTHESIS AND NUCLEOPHILIC SUBSTITUTIONS OF 3-ALKYL-5-CHLOROISOXAZOLES
Stevens, R. V.,Albizati, K. F.
, p. 4587 - 4590 (2007/10/02)
A 3-alkyl-5-chloroisoxazole synthesis is described based on the cycloaddition of nitrile oxides to 1,1-dichloroethylene, an inexpensive dipolarophile.Substitution of the chloride in these adducts by various nucleophiles is also described.
