An Efficient Multicomponent Synthesis of Highly Functionalized Cyclopentenes

Abstract

An efficient, one-pot and multicomponent synthesis of dialkyl 5,5-dicyano-3-aryl-2-cyclopentene-1,2-dicarboxylates is described. A mixture of a phenacyl bromide, malononitrile, and a dialkyl acetylenedicarboxylate in the presence of triphenylphosphine and triethylamine undergo a smooth addition reaction in absolute ethanol at ambient temperature to afford the highly functionalized cyclopentenes in good to excellent yields.

Chemoselective and one-pot synthesis of novel coumarin-based cyclopenta[c]pyrans via base-mediated reaction of α,β-unsaturated coumarins and β-ketodinitriles

“…The mechanism of the rst step including b-ketodinitriles formation is known. [32][33][34][35][36][37][38]…”

Mo (CO)6‐assisted Pd‐supported magnetic graphene oxide‐catalyzed carbonylation‐cyclization as an efficient way for the synthesis of 4(3H)‐quinazolinones

“…Palladium‐catalyzed oxidative insertion reaction of isocyanide with anthranilamide, carboxylic acids and amines, the carboxylation of ortho C–H bonds in anilides leading to N ‐acyl anthranilic acids and then treatment with anilines in the presence of PCl 3 , and the reaction of nitriles with lithiated anthranilamides are reported for the preparation of this class or compounds. In addition, other methods including microwave‐assisted condensation of anthranilic acids, oxidative reaction between benzyl halides, isatoic anhydride and primary amines, and the condensation of imidates with anthranilic acids, are reported for this purpose. Amine‐induced thermal rearrangement of iminobenzoxazines, phosphine‐catalyzed intramolecular aza‐Wittig reaction, copper iodide‐catalyzed reaction between anthranilamide, and terminal alkynes and azides have also been used for the synthesis of 4(3 H )‐quinazolinone.…”

Ruthenium‐Catalyzed Synthesis of Quinazolinones through Hydrogen Transfer and Cyclization

“…Much effort has been devoted to synthesizing quinazolinones because of their widespread applications. Over the past years, syntheses of quinazolinones commonly used oxidation/cyclization reactions of 2‐aminobenzamides with aldehydes, benzyl halides, benzyl alcohols, or orthoesters In 2005, Liu and co‐workers reported the microwave promoted two‐step reaction sequence combining anthranilic acids, carboxylic acids, and amines (Scheme a). While these synthetic methods have a few limitations such as the requirement for higher reaction temperature and many of them require stoichiometric or excess strong oxidants such as DDQ, CuCl 2 , MnO 2 , KMnO 4 and I 2 , and some reaction substrates are more complicated.…”