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 1, 1986 DOI: 10.1248/cpb.34.1628 via OpenAlex
Summary
AI-generated from the abstractA convenient one-step procedure synthesizes 1-aryl-2-nitro-3-(3,4,5-trimethoxyphenyl)propenes by reacting 1,2,3-trimethoxy-5-(2-nitroethyl)benzene with aromatic or heterocyclic aldehydes. These compounds can be reduced to yield new mescaline derivatives. As an example, 1-(3-indolyl)-2-amino-3-(3,4,5-trimethoxyphenyl)propane, which combines structural features of both mescaline and tryptamine, was prepared.
Study at a glance
| Characteristics | Synthetic chemistry paper Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Tryptamine Nitro Aryl Benzene |
| Citations | 7 |
| Key finding | A one-step reaction produces 1-aryl-2-nitro-3-(3,4,5-trimethoxyphenyl)propenes that can be reduced to new mescaline derivatives, exemplified by a compound merging mescaline and tryptamine structures. |
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.