Synthesis and structural properties of 2-([2.2]paracyclophanyl)-2,3-dihydroquinazolines by cyclocondensation of 2-aminoaryl-benzimidamides with 4-formyl[2.2]paracyclophane catalyzed efficiently by iodine

Abstract

Technical iodine was found to catalyze the condensation between 2-aminoarylbenzimidamide derivatives (1a-i) and 4-formyl[2.2]paracyclophane (2) in absolute ethanol under mild conditions to afford 2-([2.2]paracyclophanyl)-4-arylamino-2,3-dihydroquinazoline derivatives (3a-i) in good yields and with high diastereoselectivity. The obtained products were oxidized easily by KMnO 4 to yield the corresponding 2-([2.2]paracyclophanyl)-4-arylaminoquinazoline derivatives (6a-g). The structure of 3b was conformed by X-ray crystallography.

C,N‐Diarylformamidines as Valuable Building Blocks in the Synthesis of Heterocyclic Compounds

“…By a similar technique, El-Shaieb in 2009 with co-authors [42] presented a method for the synthesis of aminoquinazolines 59 by aminoarylbenzamidine reaction 1'' and 4formyl The same group of scientists in 2009 [43] investigated the reaction of 2-aminoarylbenzimidamides 1'' with isatoic anhydride 60. It was found that as a result of boiling these substrates in absolute ethanol for 2-3 hours, 2-(2-aminophenyl)-4-arylquinazoline derivatives 61 are formed with a yield of 67-79 % (Scheme 46).…”

A General and a Simple Synthesis of {4-[(Z)-4-(Arylimino)-3,4-Dihydroquinazolin-2(1H)-Ylidene]Cyclohexa-2,5-Dien-1-Ylidene} Malononitrile from the Reaction of 2-Amino-N′-Arylbenzimidamides with 7,7,8,8-Tetracyanoquinodimethane

“…[2][3][4][5] These findings prompted us to design different quinazoline derivatives for further pharmacological tests. [6][7][8] Unfortunately, synthetic methods for the elaboration of this system are not general in scope, and involve multistep, and often lowyielding, reaction sequences. Different one-pot syntheses for quinazoline derivatives have been described, but they require either high temperature or must be affected in a sealed tube at high temperature.…”