Multicomponent Reactions Involving Arynes, Quinolines, and Aldehydes

Abstract

The multicomponent reaction involving arynes, quinolines, and aldehydes leading to the diastereoselective synthesis of benzoxazino quinoline derivatives in good yields proceeding via 1,4-zwitterionic intermediates is reported. In addition, the synthetic potential of various carbonyl compounds in this reaction as well as the utility of isoquinoline as the nucleophilic trigger has been examined.

Reactions of hexadehydro-Diels–Alder benzynes with structurally complex multifunctional natural products

“…Quinidine ( 50 ) and quinine ( 54 ) both meet this criterion. Engagement with a benzyne could occur via: the quinoline nitrogen 30 , insertion into the hydroxylic O–H bond 15 , dihydrogen transfer from either the secondary alcohol or one of the (four) pairs of eclipsed H–CC–H units 15 , Alder ene reaction of the alkene 31 , 4π+2π cycloaddition with the anisole-like moiety 32 , or nucleophilic attack by the bridgehead tertiary amine (Figs. 2–4).…”

Transition-Metal-Free Synthesis of Benzo-Fused Five- and Six-Membered Heterocycles Employing Arynes

“…electrophilic component [78]. Thus, the reaction of quinoline and arynes with aldehydes resulted in the formation of benzoxazino quinoline derivatives 113 as an inseparable mixture of diastereomers in good yield and excellent diastereoselectivity (Scheme 56) [79]. In all cases, the spirooxazino (iso)quinoline derivatives 112 were formed in moderate to good yields and moderate diastereoselectivity (Scheme 55).…”

An Efficient One‐Pot Four‐Component Synthesis of Some New Spirooxindole Dihydropyridine Using Alum as a Heterogeneous Green Catalyst

“…Multicomponent [32][33][34][35][36][37] and domino [38,39] reactions are powerful tools in the modern drug discovery process in terms of lead finding and lead optimization.…”