9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid

The synthesis of the compound 9,10-dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic acid (<b>4</b>) was described for the first time using a reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline and phenyl-substituted thiodiacetic anhydride...

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Main Authors: Valentin Petrov, Teodora Aleksandrova, Aleksandar Pashev
Format: Article
Language:English
Published: MDPI AG 2025-01-01
Series:Molbank
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Online Access:https://www.mdpi.com/1422-8599/2025/1/M1955
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author Valentin Petrov
Teodora Aleksandrova
Aleksandar Pashev
author_facet Valentin Petrov
Teodora Aleksandrova
Aleksandar Pashev
author_sort Valentin Petrov
collection DOAJ
description The synthesis of the compound 9,10-dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic acid (<b>4</b>) was described for the first time using a reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline and phenyl-substituted thiodiacetic anhydride <b>3</b>. The reaction proceeded in excellent yield and furnished the compound <b>4</b> as a single diastereomer. The structure and relative configuration of <b>4</b> was elucidated using a combination of spectroscopic techniques–<sup>1</sup>H, <sup>13</sup>C, COSY, HSQC, HMBC, and NOESY NMR spectra, as well as elemental analysis.
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issn 1422-8599
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publishDate 2025-01-01
publisher MDPI AG
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series Molbank
spelling doaj-art-c01ba18712fb431fa8b2c7442f1bfa842025-08-20T02:42:28ZengMDPI AGMolbank1422-85992025-01-0120251M195510.3390/M19559,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic AcidValentin Petrov0Teodora Aleksandrova1Aleksandar Pashev2Department of Chemistry and Biochemistry, Faculty of Pharmacy, Medical University, Pleven, 1 St. Kliment Ohridski Street, 5800 Pleven, BulgariaDepartment of Chemistry and Biochemistry, Faculty of Pharmacy, Medical University, Pleven, 1 St. Kliment Ohridski Street, 5800 Pleven, BulgariaDepartment of Chemistry and Biochemistry, Faculty of Pharmacy, Medical University, Pleven, 1 St. Kliment Ohridski Street, 5800 Pleven, BulgariaThe synthesis of the compound 9,10-dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic acid (<b>4</b>) was described for the first time using a reaction between 6,7-dimethoxy-3,4-dihydroisoquinoline and phenyl-substituted thiodiacetic anhydride <b>3</b>. The reaction proceeded in excellent yield and furnished the compound <b>4</b> as a single diastereomer. The structure and relative configuration of <b>4</b> was elucidated using a combination of spectroscopic techniques–<sup>1</sup>H, <sup>13</sup>C, COSY, HSQC, HMBC, and NOESY NMR spectra, as well as elemental analysis.https://www.mdpi.com/1422-8599/2025/1/M19556,7-dimethoxy-3,4-dihydroisoquinolinethiodiacetic anhydride[1,4]thiazino[3,4-a]isoquinoline
spellingShingle Valentin Petrov
Teodora Aleksandrova
Aleksandar Pashev
9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
Molbank
6,7-dimethoxy-3,4-dihydroisoquinoline
thiodiacetic anhydride
[1,4]thiazino[3,4-a]isoquinoline
title 9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
title_full 9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
title_fullStr 9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
title_full_unstemmed 9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
title_short 9,10-Dimethoxy-4-oxo-1-phenyl-1,3,4,6,7,11b-hexahydro-[1,4]thiazino[3,4-a]isoquinoline-1-carboxylic Acid
title_sort 9 10 dimethoxy 4 oxo 1 phenyl 1 3 4 6 7 11b hexahydro 1 4 thiazino 3 4 a isoquinoline 1 carboxylic acid
topic 6,7-dimethoxy-3,4-dihydroisoquinoline
thiodiacetic anhydride
[1,4]thiazino[3,4-a]isoquinoline
url https://www.mdpi.com/1422-8599/2025/1/M1955
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AT teodoraaleksandrova 910dimethoxy4oxo1phenyl1346711bhexahydro14thiazino34aisoquinoline1carboxylicacid
AT aleksandarpashev 910dimethoxy4oxo1phenyl1346711bhexahydro14thiazino34aisoquinoline1carboxylicacid