Mukherjee, Attreyee; Mahalanabis, Kumar K. published the artcile< Systematic study on acylation of methyl 3-aminocrotonate with acid chlorides of aliphatic, aromatic and α,β-unsaturated acids: a comparative evaluation of the preference for regio- and stereoselectivity vis-a'-vis 3-aminocrotononitrile>, Name: (E)-Cinnamoyl chloride, the main research area is methyl aminocrotonate regioselective diastereoselective acylation.
Acylation of Me 3-aminocrotonate in benzene with a variety of aliphatic and aromatic acid chlorides including α,β-unsaturated acid chloride in the presence of an added organic base, (either pyridine or triethylamine) was reported. The preferred N, C-site selectivity in these reactions was compared with the terminal selectivity of the products obtained previously on acylation of Me 3-aminocrotononitrile. A strong preference either for N- or C- selectivity in N, C-acylation was observed for both Me 3-aminocrotonate and Me 3-aminocrotononitrile based on the choice of acid chlorides and added organic base. Interestingly, irresp. of the enamine Me 3-aminocrotonate or Me 3-aminocrotononitrile, acylation with α,β-unsaturated acid chlorides in the presence of triethylamine afforded 3,4-dihydropyridin-(2H)-one via [3.3] sigmatropic rearrangement of the corresponding intermediary N(E)-enamide. Accrued results showed Me 3-aminocrotonate to be a better precursor for preparation of enamides (N-acylated products) whereas 3-aminocrotononitrile was found to be a preferred choice for preparation of enaminones (C-acylated products). An attempt was made to offer a preliminary theor. interpretation for observed site selectivity.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 17082-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C9H7ClO, Name: (E)-Cinnamoyl chloride.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics