A versatile synthesis of 1-aryl-2-nitro-3-(3,4,5-trimethoxyphenyl)propenes as precursors of novel mescaline derivatives.
Chemical and Pharmaceutical Bulletin – January 01, 1986
Source: OpenAlex
Summary
A convenient one-step synthesis yielded 15 new mescaline derivatives, showcasing a novel reaction between 1,2,3-trimethoxy-5-(2-nitroethyl)benzene and various aromatic or heterocyclic aldehydes. This process produced 1-aryl-2-nitro-3-(3,4,5-trimethoxyphenyl)propenes, which can be easily reduced. Notably, the compound 1-(3-indolyl)-2-amino-3-(3,4,5-trimethoxyphenyl)propane combines key structural elements of both mescaline and tryptamine. This advancement in organic chemistry could enhance the understanding of benzodiazepine derivatives and their pharmacological applications.
Abstract
A convenient one-step procedure to synthesize the title compounds (3a-v) by the reaction between 1, 2, 3-trimethoxy-5-(2-nitroethyl)benzene (1) and aromatic or heterocyclic aldehydes is reported. The obtained 1-aryl-2-nitro-3-(3, 4, 5-trimethoxyphenyl)propenes can easily be reduced to provide new mescaline derivatives. As an example, 1-(3-indolyl)-2-amino-3-(3, 4, 5-trimethoxyphenyl)propane (4), which contains in the same molecule the structural features of both mescaline and tryptamine, has been prepared.