Stereocontrolled Synthesis of 3,6-Dimethyl- 2,3,6,7,12,12a-hexahydropyrazino[1,2-b]-β- carboline-1,4-diones

Prescribed drugs containing nitrogen heterocycles: an overview

“…The core structure in talalafil is a tetrahydro-β-carboline. Its synthesis is relatively straightforward and is relied on the work of Anand 126 and co-workers via the straightforward multistep synthesis using four key framework, namely, d -tryptophan methyl ester 95, market accessible piperonal 96, chloroacetyl chloride, and methylamine. 127 …”

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].…”

Synthesis of 1‐(m‐Hydroxybenzyl)‐Substituted 1,2,3,4‐Tetrahydroisoquinoline‐3‐carboxylic Acid Derivatives as Opioid Peptide Mimetics − Unexpected Amide Bond Cleavages under Mild Conditions

“…Yield 0.37 g or 60%, oil; R f (EtOAc/ cyclohexane 1:1) 0.57; R f (EtOAc/cyclohexane 1:4) 0. 16 23 mmol) in TFA containing 5% of water (5 mL) was stirred for 15 min at room temp. The solvent was evaporated, acetic acid (10 mL) was added, and the mixture was lyophilized.…”

“…and protected from daylight, as described. [16] After a reaction time of 1 night, additional Z-Gly-OH (0.09 g, 0.44 mmol) and EDC (0.08 g, 0.44 mmol) were added. The reaction was allowed to continue for another 3 to 4 days.…”