17952-72-6Relevant academic research and scientific papers
A rapid, mild, efficient, and solvent-free Friedel-Crafts acylation of N-acetyltetrahydroharmine
Begum, Sabira,Hassan, Syed Imran,Siddiqui, Bina S.
, p. 23 - 39 (2005)
The first solid-phase, rapid, and mild synthesis of 10-acyl and 12-acyl analogues of N-acetyltetrahydroharmine by Friedel-Crafts acylation has been developed. The products were obtained in high overall yields. The method also results in the high-yield synthesis of natural product jafrine.
Jafrine, a novel and labile β-carboline alkaloid from the flowers of Tagetes patula
Faizi, Shaheen,Naz, Aneela
, p. 6185 - 6197 (2002)
An inherently unstable and structurally novel tetrahydro β-carboline alkaloid, (+) jafrine (1) was isolated from the petroleum ether extract of Tagetes patula flowers. Its structure and stereochemistry has been determined with the help of spectroscopic analysis and the synthesis of racemate, (±) jafrine starting from available (±) tetrahydroharmine (2). The effect of solvent polarity on the ratio of amide rotamers of jafrine during NMR studies is discussed. The transformation of jafrine as well as 4-N-acetyl tetrahydroharmine (3), into 2-acetyl tryptamine derivatives by auto-oxidation was observed and its detail is presented. This process may be used as a synthetic tool for the preparation of tryptamine derivatives.
