The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates wh...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.44 |
| _version_ | 1818665037678510080 |
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| author | Marina V. Goryaeva Yanina V. Burgart Marina A. Ezhikova Mikhail I. Kodess Viktor I. Saloutin |
| author_facet | Marina V. Goryaeva Yanina V. Burgart Marina A. Ezhikova Mikhail I. Kodess Viktor I. Saloutin |
| author_sort | Marina V. Goryaeva |
| collection | DOAJ |
| description | The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate. |
| first_indexed | 2024-12-17T05:42:16Z |
| format | Article |
| id | doaj.art-f5d15db81f8f45ba87aefe4b11de779e |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T05:42:16Z |
| publishDate | 2015-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f5d15db81f8f45ba87aefe4b11de779e2022-12-21T22:01:24ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-03-0111138539110.3762/bjoc.11.441860-5397-11-44The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocyclesMarina V. Goryaeva0Yanina V. Burgart1Marina A. Ezhikova2Mikhail I. Kodess3Viktor I. Saloutin4Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy St., 620137 Ekaterinburg, RussiaPostovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy St., 620137 Ekaterinburg, RussiaPostovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy St., 620137 Ekaterinburg, RussiaPostovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy St., 620137 Ekaterinburg, RussiaPostovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoy St., 620137 Ekaterinburg, RussiaThe interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.https://doi.org/10.3762/bjoc.11.445-aminotetrazolecyclisationdiethyl 2-ethoxymethylidenemalonate2-ethoxymethylidene-3-oxo estersethyl 2-ethoxymethylidenecyanoacetate |
| spellingShingle | Marina V. Goryaeva Yanina V. Burgart Marina A. Ezhikova Mikhail I. Kodess Viktor I. Saloutin The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles Beilstein Journal of Organic Chemistry 5-aminotetrazole cyclisation diethyl 2-ethoxymethylidenemalonate 2-ethoxymethylidene-3-oxo esters ethyl 2-ethoxymethylidenecyanoacetate |
| title | The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles |
| title_full | The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles |
| title_fullStr | The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles |
| title_full_unstemmed | The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles |
| title_short | The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles |
| title_sort | reactions of 2 ethoxymethylidene 3 oxo esters and their analogues with 5 aminotetrazole as a way to novel azaheterocycles |
| topic | 5-aminotetrazole cyclisation diethyl 2-ethoxymethylidenemalonate 2-ethoxymethylidene-3-oxo esters ethyl 2-ethoxymethylidenecyanoacetate |
| url | https://doi.org/10.3762/bjoc.11.44 |
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