Synthesis of some indolyl Mannish bases

Abstract

Mannich reaction is of great scope and utility , employed in organic synthesis of natural compounds such as peptides ,nucleotides , antibiotics , and alkaloids ,other applications are in agrochemicals such as plant growth regulators ,paint and polymer chemistry ,catalysts and cross linking .In this work derivatives of indole-3-butyric acid ,and 2-phenylindole were prepared as manich bases by the nucleophilic addition of an amine to carbonyl group of formaldehyde followed by dehydration to Schiff base .The Schiff base is an electrophile which react in the second step in a nucleophilic addition with a compound containing an acidic proton (indole-3-butyric acid ,and 2-phenylindole) .The compounds were prepared according to a well stablished literature methods and identities of these compounds were confirmed by IR , UV, MS spectrophotometer and TLC analysis. Mechanism of reaction is given and discussed in chapter three. Detailed spectral (IR, MS) analysis of target compounds was given. The functional groups were assigned to proper absorption bands, a variation in the number of peaks , positions and increasing or decreasing in the values of bonds were noticed according to various effects, such as resonance effects, conjugation effects etc...