Journal
MOLECULES
Volume 26, Issue 20, Pages -Publisher
MDPI
DOI: 10.3390/molecules26206126
Keywords
isoquinoline; aza-Michael addition; heterocycles
Funding
- National Chi Nan University
- Ministry of Science and Technology, Taiwan [107-2113-M-260-006-and 106-2113-M-260-002-]
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It was found that 4-hydroxy-2-butenoic ester could not react with 3,4-dihydro-isoquinoline. Reactions of gamma-mercapto-alpha,beta-unsaturated esters and -unsaturated amide with 3,4-dihydroisoquinolines provided thiazolo[2,3-alpha]isoquinoline derivatives with good yields and significant diastereomeric selectivity, with the mechanism of the crucial reaction being discussed.
It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of gamma-mercapto-alpha,beta-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-alpha]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed.
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