31883-80-4Relevant academic research and scientific papers
Regioselective palladium(II)-catalyzed synthesis of five- or seven-membered ring lactones and five-, six- or seven-membered ring lactams by cyclocarbonylation methodology
El Ali, Bassam,Okuro, Kazumi,Vasapollo, Giuseppe,Alper, Howard
, p. 4264 - 4270 (1996)
2-Allylphenols react with carbon monoxide and hydrogen in the presence of catalytic quantities of a cationic palladium(II) complex [(PCy3)2Pd(H)(H2O)]+BF4- or palladium acetate and 1,4-bis(diphenylpho
Photochemical reactions of N-(2-halogenoalkanoyl) derivatives of anilines
Nishio, Takehiko,Asai, Hidenori,Miyazaki, Takenori
, p. 1475 - 1483 (2007/10/03)
The photochemical reactions of 2-substituted N-(2-halogenoalkanoyl) derivatives 1 of anilines and 5 of cyclic amines are described. Under irradiation, 2-bromo-2-methylpropananilides 1a-e undergo exclusively dehydrobromination to give N-aryl-2-methylprop-2-enamides (= methacrylanilides) 3a-e (Scheme 1 and Table 1). On irradiation of N-alkyl- and N-phenyl-substituted 2-bromo-2-methylpropananilides 1f-m, cyclization products, i.e. 1,3-dihydro-2H-indol-2-ones (= oxindoles) 2f-m and 3,4- dihydroquinolin-2(1H)-ones (= dihydrocarbostyrils) 4f-m, are obtained, besides 3f-m. On the other hand, irradiation of N-methyl-substituted 2- chloro-2-phenylacetanilides 1o-q and 2-chloroacetanilide 1r gives oxindoles 2o-r as the sole product, but in low yields (Scheme 3 and Table 2). The photocyclization of the corresponding N-phenyl derivatives 1s-v to oxindoles 2s-v proceeds smoothly. A plausible mechanism for the formation of the photoproducts is proposed (Scheme 4). Irradiation of N-(2-halogenoalkanoyl) derivatives of cyclic amines 5a-c yields the cyclization products, i.e. five- membered lactams 6a, b, and/or dehydrohalogenation products 7a,c and their cyclization products 8a,c, depending on the ring size of the amines (Scheme 5 and Table 3).
