Utility of 2-cyano-3-phenyl-2-propenoyl chloride as Michael’s acceptor in heterocyclic synthesis with mono- and bi-dentate nucleophiles

3-Aryl/hetaryl-2-cyanoacryloyl chlorides: Synthesis and Reactions with Binucleophiles Targeting Heterocycles

“…Treating the acrylic acid derivatives 5 with thionyl chloride acquired the targeted acid chlorides 6 (Scheme 1). [2][3][4][10][11][12]…”

“…On the other hand, reaction of acid chlorides 6a, 6i and 6j with benzoylhydrazine yielded N,N'diacylhydrazine 12 which, upon heating with phosphorus oxychloride produced the corresponding dehydrating product, 1,3,4-oxadiazole derivative 13 (Scheme 5). [3,11,12] Scheme 5. Reaction of acid chlorides with benzoylhydrazine.…”

“…Noteworthy, the acid chlorides 6 have been successfully transformed into benzoxazinone derivatives 43 via its treating with anthranilic acid or its derivatives under basic conditions affording the benzamide derivatives 42 followed by ring closure using acetic anhydride (Scheme 17). [1][2][3][10][11][12] Scheme 17. Reaction of acid chlorides with anthranilic acid derivatives.…”

“…Recently, 2-cyanopropenoyl chlorides have attracted a great attention due to their medicinal importance as a building block for various biological and pharmaceutical significant heterocyclic skeletons like benzimidazoles[1-3], benzoxazoles[4-6], benzothiazoles[7-9], benzoxazines [10], oxadiazoles [11], and pyrazoles [12], in addition to a wide variety of valuable fused heterocyclic systems (Fig. 1).…”