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Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines.

ABSTRACT: It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-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-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was discussed.

SUBMITTER: Huang SH

PROVIDER: S-EPMC8537374 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines.

Huang Sheng-Han SH Huang Wan-Yu WY Zhang Guo-Lun GL Yang Te-Fang TF

Molecules (Basel, Switzerland) 20211011 20

It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-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-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric selectivity. The mechanism of the crucial reaction was ...[more]

PMID: 34684705

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