The synthesis of new heterocyclic bridged ring systems. Analogs of tetrahydro-β-carbolines

Traceless and Stereoselective Synthesis of Tetrahydro-β-carbolinethiohydantoins by Microwave Irradiation

“…Heterocycles are versatile molecular scaffolds, on to which meaningful structural diversity can be introduced to vary the stereochemical and physicochemical properties of the resulting compounds, thus tailoring them for better membrane transport and receptor binding in biological systems. Tetrahydro-β-carbolines are one such class of semirigidized tricyclic heterocycles, which are found to occur as mammalian and plant alkaloids, like jafraine, exhibiting a wide range of biological activities. − The tetrahydro-β-carbolines such as demethoxyfumitremorgins have been isolated from the fungal species, some of which have been found to exhibit antiviral, topoisomerase II inhibiting, and protein kinase and cell cycle inhibiting activities (Figure ). Because of their potential biological properties, these tetra- and polycyclic β-carbolines have been synthesized by classical , as well as solid-phase − methods.…”

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

“…designed an efficient route for the synthesis of few analogues of complex tetrahydro‐β‐carboline alkaloids, Arborescidine B and Arborescidine C (Scheme ). Indole was condensed with N ‐benzyl‐3‐piperidinone in the presence of sodium methoxide to get indolyl‐3‐ N ‐benzyltetrahyropyridine 222 , which was reduced and debenzylated in single step to synthesize Pictet‐Spengler substrate indolylpiperidine 223 . Pictet‐Spengler condensation of piperidine 223 with various aldehydes afforded a diastereomeric mixture of 224 and 225 .…”

Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

“…Among the latter, many compounds are important drugs, including benzyltetrahydroisoquinoline alkaloids which are synthesized via enzymatic Pictet-Spengler reaction, i.e., condensation of aldehydes with 2-arylethanamines 58 with formation of tetrahydroisoquinolines 57 (Scheme 15). The amine component may be derivatives of phenylalkanamines [47][48][49][50][51] [52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67], amines of the naphthalene series [68], and aminoalkyl derivatives of heterocyclic compounds [69,70]. If X = O, the corresponding 1,2-oxazines, 1,2-oxazepines, and 1,2-oxazocines are obtained [71].…”