Nucleophilic Aromatic Substitution Reactions of meso‐Bromosubporphyrin: Synthesis of a Thiopyrane‐Fused Subporphyrin

meso‐Bromosubporphyrin undergoes nucleophilic aromatic substitution (S_NAr) reactions with arylamines, diarylamines, phenols, ethanol, thiophenols, and n‐butanethiol in the presence of suitable bases to provide the corresponding substitution products. The S_NAr reactions also proceed well with pyrrole, indole, and carbazole to provide substitution products in moderate to good yields. Finally, the S_NAr reaction with 2‐bromothiophenol and subsequent intramolecular peripheral arylation reaction affords a thiopyrane‐fused subporphyrin.     

A Facile Method for Nucleophilic Aromatic Substitution of Cyclic Amine

The expeditious solventless nucleophilic aromatic substitution using microwaves is described. A non-conventional synthetic procedure has been developed where basic alumina has been used as energy transfer medium under Microwave Irradiation (MW1). The results were compared with those obtained by the classical method. This rapid and environmentally benign method avoids the use of excess solvents and toxic bases usually employed in the process make this procedure very attractive for synthesis.