An Unusual and Chemoselective Reduction of Ester Grouping in Nsubstituted-3-acetylindoles by Sodium Borohydride

l-Proline-Catalyzed Three-Component Reaction of 4-Chloro-3-formylcoumarin, Sodium Sulfide, and α-Halo Ketones: A Direct Approach to Thieno[3,2-c]coumarins

“…Based on the structures of the isolated products and previous reports in the literature, 56 57 58 a plausible reaction mechanism for the formation of 5a is proposed, as shown in Scheme 3 . The dropwise addition of 4-chloro-3-formylcoumarin ( 1 ) to the aqueous sodium sulfide solution generates sodium 3-formyl-2-oxo-2 H -chromene-4-thiolate ( 3 ).…”

Chemistry of 3-cyanoacetyl indoles: synthesis, reactions and applications: a recent update

“…39 In 2013, a facial method for the synthesis of 3-cyanoacetyl indole derivatives 1 in 84-95% yields reported by the reaction of indoles 2, cyanoacetic acid and propanoic anhydride at 65-75 °C for 7 min (Scheme 6). 40…”

Design, synthesis, theoretical study, antioxidant, and anticholinesterase activities of new pyrazolo-fused phenanthrolines

“…A possible mechanism for this method begins with a Knoevenagel reaction between an aromatic aldehyde (1a-m) and malononitrile (4), using L-proline as the catalyst, which in its zwitterion form extracts the proton of 4, forming the respective carbanion (4 ′ ), which then attacks the protonated aldehyde (1 ′ ), forming the corresponding intermediate (1 ′′ ) that loses water to produce molecule 13 (see Scheme 3B). 39 Simultaneously, compound 2 reacts with ammonium acetate to produce imine 11, which by isomerization is transformed into enamine 12, which subsequently undergoes a Michael reaction with compound 13 to produce molecule 14, which by isomerization transforms into compound 8, which aer cyclization, isomerization and aromatization generates the nal product 5a-m with yields of up to 59%. 38 Structurally, these nal compounds have a 2amino-3-cyanoquinoline system that is of great interest for both reactivity and biological applications.…”