N-Heterocyclic systems are a constituent part of many products of pharmaco-biological interest, a fact that is reflected in extensive study chapters of organic chemistry, mainly due to their dissemination in nature, where they are usually found as fundamental structural scaffolds of biologically active molecules such as alkaloids and antibiotics, as well as of many synthetic drugs that are currently used as anticancer agents, antipsychotics, antimuscarinics, among other important applications. Among the great variety of heterocyclic nitrogenous systems of biological importance, phenanthridines have aroused great interest in the scientific community and particularly in organic chemists, due to the wide spectrum of activities they exhibit. Many phenanthridine derivatives found in nature have proven to be effective anticancer agents, motivating the design and implementation of the synthetic arsenal available for their preparation: versatile and novel synthetic routes leading to the development of structurally richer derivatives with improved biological activities and low toxicity. For this reason, it is important to obtain N-heterocycles compounds in a simple and environmentally friendly way, using synthetic routes in accordance with green chemistry. In this contribution, we present a sustainable synthesis of new 6-arylphenanthridines through Pictet-Spengler reaction starting from [1,1'-biphenyl]-2-amine derivative and aromatic aldehydes in choline chloride/zinc chloride eutectic mixture and [Bmim]PF6 as new reaction media for this approach.
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Synthesis of novel 6-arylphenanthridines via sequential Suzuki-Miyaura and Pictet-Spengler reactions under green chemistry conditions
Published:
03 November 2021
by MDPI
in 7th International Electronic Conference on Medicinal Chemistry
session Fighting cancers
Abstract:
Keywords: Green chemistry, Phenanthridines, Chemical synthesis, Pictet-Spengler