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Alekseeva, Kseniya A.; Fedoseeva, Milana A.; Bakhanovich, Olga V.; Khrustalev, Victor N.; Potkin, Vladimir I.; Zhou, Hongwei; Nikitina, Eugenia V.; Zaytsev, Vladimir P.; Zubkov, Fedor I.
Journal of organic chemistry, 03/2024, Letnik: 89, Številka: 5Journal Article
One-pot synthesis of tetrahydro-β-carbolines, fused with an isoindole core, was proposed starting from maleic anhydride and azomethines easily available from tryptamines and 3-(hetaryl)acroleins. This sequence includes four key steps: an acylation of the aldimine with maleic anhydride, a Pictet–Spengler cyclization, an intramolecular Diels–Alder reaction, and a concluding 1,3-H shift. As a result, six- or seven-nuclear alkaloid-like heterocyclic systems, containing a benzo1,2indolizino8,7-bindole fragment annulated with furan, thiophene, or pyrrole, are formed in a diastereoselective manner.
