Open AccessSynthesis, Characterization, and Crystal Structure of Some New Tetrahydroisoquinolines and Related Tetrahydrothieno[2,3-c]isoquinolines
Author(s) -
Islam S. Marae,
Etify A. Bakhite,
O. S. Moustafa,
M. S. Abbady,
Shaaban K. Mohamed,
Joel T. Mague
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c00050
Subject(s) - chemistry , sodium ethoxide , aryl , crystal structure , acetic acid , medicinal chemistry , ethanol , intramolecular force , molecule , stereochemistry , organic chemistry , alkyl
The starting compounds 7-acetyl-8-aryl-4-cyano-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline(2 H )-3-thiones 3a,b were synthesized and reacted with some N -aryl-2-chloroacetamides 4a-e in the presence of sodium acetate to produce 7-acetyl-8-aryl-3-( N- arylcarbamoylmethylsulfanyl)-4-cyano-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinolines 5a-g . Upon heating in ethanol containing sodium ethoxide, they underwent intramolecular Thorpe-Zeigler cyclization, affording the corresponding 7-acetyl-1-amino-6-aryl-2-( N -arylcarbamoyl)-5,8-dimethyl-8-hydroxy-6,7,8,9-tetrahydrothieno[2,3- c ]isoquinolines 6a-g . Compounds 6c,g,f were converted into the corresponding 1-(1-pyrrolyl) derivatives 7a-c by heating with 2,5-dimethoxytetrahydrofuran in glacial acetic acid. Structures of all synthesized compounds were characterized by elemental and spectral analyses. Also, the crystal structure of compounds 5a was determined by X-ray diffraction analysis.