25755-83-3Relevant articles and documents
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)
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.
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.
A novel strategy for the synthesis of thermally stable and apoptosis-inducing 2,3-dihydroazetes
Smetanin, Ilia A.,Novikov, Mikhail S.,Agafonova, Anastasiya V.,RostovskII, Nikolai V.,Khlebnikov, Alexander F.,Kudryavtsev, Igor V.,Terpilowski, Maxim A.,Serebriakova, Maria K.,Trulioff, Andrey S.,Goncharov, Nikolay V.
supporting information, p. 4479 - 4487 (2016/06/06)
A general and concise approach to thermally and hydrolytically stable alkyl 2,3-dihydroazete-2,3-di-/2,2,3-tricarboxylates from alkyl 2-bromoazirine-2-carboxylates or 4-bromo-5-alkoxyisoxazoles is reported. The synthesis involves the formation of 2-azabut
