Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
It was found that 4-hydroxy-2-butenoic ester <b>(11)</b> could not react with 3,4-dihydro-isoquinoline (<b>4a</b>). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (<b>18)</b> and -unsaturated amide (<b>19)</b> with 3,4-dihydroisoqui...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/20/6126 |
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| author | Sheng-Han Huang Wan-Yu Huang Guo-Lun Zhang Te-Fang Yang |
| author_facet | Sheng-Han Huang Wan-Yu Huang Guo-Lun Zhang Te-Fang Yang |
| author_sort | Sheng-Han Huang |
| collection | DOAJ |
| description | It was found that 4-hydroxy-2-butenoic ester <b>(11)</b> could not react with 3,4-dihydro-isoquinoline (<b>4a</b>). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (<b>18)</b> and -unsaturated amide (<b>19)</b> with 3,4-dihydroisoquinolines (<b>4</b>) 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. |
| first_indexed | 2024-03-10T06:21:06Z |
| format | Article |
| id | doaj.art-6fe3eafac06c4534966527e202649bc2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T06:21:06Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6fe3eafac06c4534966527e202649bc22023-11-22T19:18:23ZengMDPI AGMolecules1420-30492021-10-012620612610.3390/molecules26206126Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolinesSheng-Han Huang0Wan-Yu Huang1Guo-Lun Zhang2Te-Fang Yang3Department of Applied Chemistry, National Chi Nan University, Puli, Nantou 545, TaiwanDepartment of Applied Chemistry, National Chi Nan University, Puli, Nantou 545, TaiwanDepartment of Applied Chemistry, National Chi Nan University, Puli, Nantou 545, TaiwanDepartment of Applied Chemistry, National Chi Nan University, Puli, Nantou 545, TaiwanIt was found that 4-hydroxy-2-butenoic ester <b>(11)</b> could not react with 3,4-dihydro-isoquinoline (<b>4a</b>). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (<b>18)</b> and -unsaturated amide (<b>19)</b> with 3,4-dihydroisoquinolines (<b>4</b>) 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.https://www.mdpi.com/1420-3049/26/20/6126isoquinolineaza-Michael additionheterocycles |
| spellingShingle | Sheng-Han Huang Wan-Yu Huang Guo-Lun Zhang Te-Fang Yang Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines Molecules isoquinoline aza-Michael addition heterocycles |
| title | Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines |
| title_full | Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines |
| title_fullStr | Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines |
| title_full_unstemmed | Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines |
| title_short | Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines |
| title_sort | facile synthesis of 3 substituted thiazolo 2 3 α tetrahydroisoquinolines |
| topic | isoquinoline aza-Michael addition heterocycles |
| url | https://www.mdpi.com/1420-3049/26/20/6126 |
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