Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes
Tetrahydroquinolines are important structural fragments of many biologically active compounds exhibiting antifungal, antitumor, antiviral and neurotropic properties. This paper presents methods for the synthesis of N-substituted tetrahydroquinoline-6-carbaldehydes and a study of the possibility of t...
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Saratov State University
2025-06-01
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| Series: | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
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| Online Access: | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2025/07/himiya-2025-2-128-136.pdf |
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| author | Karelina, Kristina Olegovna Potapov, Andrey Юрьевич |
| author_facet | Karelina, Kristina Olegovna Potapov, Andrey Юрьевич |
| author_sort | Karelina, Kristina Olegovna |
| collection | DOAJ |
| description | Tetrahydroquinolines are important structural fragments of many biologically active compounds exhibiting antifungal, antitumor, antiviral and neurotropic properties. This paper presents methods for the synthesis of N-substituted tetrahydroquinoline-6-carbaldehydes and a study of the possibility of their olefi nation using the Wittig and Horner – Wadsworth – Emmons methods. As a result of the interaction of N-alkyl- and N-acylhydroquinolines with the Vilsmeier – Haack complex, N-substituted tetrahydroquinoline-6-carbaldehydes have been obtained in yields of 77–85%. Olefi nation of the obtained carbaldehydes by the Wittig reaction using triphenylalkylphosphonium salts has made it possible to obtain a number of N-substituted derivatives, including: (E)-3-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)acrylonitriles, (E)-1-phenyl-3-(2,2,4- trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)prop-2-en-1-ones, ethyl (E)-3-(N-benzoyl-7-methoxy-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylate. It has been found that when this interaction is extended to N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde and N-benzyl-2,2,4-trimethyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoline-6-carbaldehyde, diffi cult-to-separate mixtures are formed, which is explained by the presence of a methylene-active benzyl group in these compounds, which in the presence of sodium methylate can enter into condensation with the aldehyde fragment. The application of the Horner – Wadsworth – Emmons reaction for the olefi nation of N-methyl- and N-benzyl-1,2,3,4-tetrahydroquinoline-6-carbaldehydes using dimethyl (cyanomethyl) phosphonate has made it possible to synthesize (E)-3-(Nmethyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile, (E)-3-(N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile and (E)-3-(-N-benzyl-2,2,4-trimethyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile with yields of 83–89%. Analysis of the ¹H NMR spectra has showed that all the synthesized olefi nation products are in the form of E-isomers. The obtained results demonstrate the potential of using the developed methods for the synthesis of new tetrahydroquinoline derivatives. |
| format | Article |
| id | doaj-art-4eea58132e06490ea1a6856cedd92c8c |
| institution | Kabale University |
| issn | 1816-9775 2541-8971 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Saratov State University |
| record_format | Article |
| series | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
| spelling | doaj-art-4eea58132e06490ea1a6856cedd92c8c2025-08-24T15:04:29ZengSaratov State UniversityИзвестия Саратовского университета. Новая серия: Серия Химия. Биология. Экология1816-97752541-89712025-06-0125212813610.18500/1816-9775-2025-25-2-128-136Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydesKarelina, Kristina Olegovna0Potapov, Andrey Юрьевич1Voronezh State University, Universitetskaya sq., 1, Voronezh, Voronezh region, 394036Voronezh State University, Universitetskaya sq., 1, Voronezh, Voronezh region, 394036Tetrahydroquinolines are important structural fragments of many biologically active compounds exhibiting antifungal, antitumor, antiviral and neurotropic properties. This paper presents methods for the synthesis of N-substituted tetrahydroquinoline-6-carbaldehydes and a study of the possibility of their olefi nation using the Wittig and Horner – Wadsworth – Emmons methods. As a result of the interaction of N-alkyl- and N-acylhydroquinolines with the Vilsmeier – Haack complex, N-substituted tetrahydroquinoline-6-carbaldehydes have been obtained in yields of 77–85%. Olefi nation of the obtained carbaldehydes by the Wittig reaction using triphenylalkylphosphonium salts has made it possible to obtain a number of N-substituted derivatives, including: (E)-3-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)acrylonitriles, (E)-1-phenyl-3-(2,2,4- trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)prop-2-en-1-ones, ethyl (E)-3-(N-benzoyl-7-methoxy-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylate. It has been found that when this interaction is extended to N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde and N-benzyl-2,2,4-trimethyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoline-6-carbaldehyde, diffi cult-to-separate mixtures are formed, which is explained by the presence of a methylene-active benzyl group in these compounds, which in the presence of sodium methylate can enter into condensation with the aldehyde fragment. The application of the Horner – Wadsworth – Emmons reaction for the olefi nation of N-methyl- and N-benzyl-1,2,3,4-tetrahydroquinoline-6-carbaldehydes using dimethyl (cyanomethyl) phosphonate has made it possible to synthesize (E)-3-(Nmethyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile, (E)-3-(N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile and (E)-3-(-N-benzyl-2,2,4-trimethyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydroquinolin-6-yl) acrylonitrile with yields of 83–89%. Analysis of the ¹H NMR spectra has showed that all the synthesized olefi nation products are in the form of E-isomers. The obtained results demonstrate the potential of using the developed methods for the synthesis of new tetrahydroquinoline derivatives.https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2025/07/himiya-2025-2-128-136.pdf1234-tetrahydroquinolinevilsmeier – haack reactionolefi nationwittig reactionhorner – wadsworth – emmons reaction |
| spellingShingle | Karelina, Kristina Olegovna Potapov, Andrey Юрьевич Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология 1 2 3 4-tetrahydroquinoline vilsmeier – haack reaction olefi nation wittig reaction horner – wadsworth – emmons reaction |
| title | Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes |
| title_full | Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes |
| title_fullStr | Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes |
| title_full_unstemmed | Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes |
| title_short | Carbonyl olefi nation of N-substituted tetrahydroquinoline-6-carbaldehydes |
| title_sort | carbonyl olefi nation of n substituted tetrahydroquinoline 6 carbaldehydes |
| topic | 1 2 3 4-tetrahydroquinoline vilsmeier – haack reaction olefi nation wittig reaction horner – wadsworth – emmons reaction |
| url | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2025/07/himiya-2025-2-128-136.pdf |
| work_keys_str_mv | AT karelinakristinaolegovna carbonylolefinationofnsubstitutedtetrahydroquinoline6carbaldehydes AT potapovandreyûrʹevič carbonylolefinationofnsubstitutedtetrahydroquinoline6carbaldehydes |