18803-02-6Relevant articles and documents
4-Alkoxy-3-cyano-2(1H)-pyridones and 5-alkoxyisoxazoles and their aryl substituted and annulated derivatives from acylketene O,S-acetals
Purkayastha,Bhat,Ila,Junjappa
, p. 641 - 643 (1995)
The title pyridones 2 and 5 and the isoxazoles 3 and 6 are obtained in moderate to good yields by cyclocondensation of the appropriate acylketene O,S-acetals 1 or 4 with cyanoacetamide and hydroxylamine hydrochloride, respectively, in the presence of sodi
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.
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
Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines
Auricchio, Sergio,Bini, Antonella,Pastormerlo, Eros,Truscello, Ada M.
, p. 10911 - 10920 (2007/10/03)
5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.