Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems
3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a,12,12a-tetrahydrobis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine-4,10-diones. The latter compounds, with a new heter...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-04-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.74 |
| _version_ | 1819295963343224832 |
|---|---|
| author | Alexander F. Khlebnikov Mikhail S. Novikov Viktoriia V. Pakalnis Roman O. Iakovenko Dmitry S. Yufit |
| author_facet | Alexander F. Khlebnikov Mikhail S. Novikov Viktoriia V. Pakalnis Roman O. Iakovenko Dmitry S. Yufit |
| author_sort | Alexander F. Khlebnikov |
| collection | DOAJ |
| description | 3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a,12,12a-tetrahydrobis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine-4,10-diones. The latter compounds, with a new heterocyclic skeleton, are the result of the coupling of two molecules of azirine and two molecules of acylketene and can be prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition of the latter to two molecules of acylketenes. |
| first_indexed | 2024-12-24T04:50:34Z |
| format | Article |
| id | doaj.art-21b1a269e51547dda5aeccff25730f93 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-24T04:50:34Z |
| publishDate | 2014-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-21b1a269e51547dda5aeccff25730f932022-12-21T17:14:33ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110178479310.3762/bjoc.10.741860-5397-10-74Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systemsAlexander F. Khlebnikov0Mikhail S. Novikov1Viktoriia V. Pakalnis2Roman O. Iakovenko3Dmitry S. Yufit4Department of Chemistry, Saint-Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, RussiaDepartment of Chemistry, Saint-Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, RussiaDepartment of Chemistry, Saint-Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, RussiaDepartment of Chemistry, Saint-Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, RussiaDepartment of Chemistry, University of Durham, Durham, South Rd., DH1 3LE, UK3-Aryl-2H-azirines react with acylketenes, generated by thermolysis of 5-arylfuran-2,3-diones, to give bridged 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-diones and/or ortho-fused 6,6a,12,12a-tetrahydrobis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine-4,10-diones. The latter compounds, with a new heterocyclic skeleton, are the result of the coupling of two molecules of azirine and two molecules of acylketene and can be prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition of the latter to two molecules of acylketenes.https://doi.org/10.3762/bjoc.10.74acylketeneazirinedomino reactionfurandione |
| spellingShingle | Alexander F. Khlebnikov Mikhail S. Novikov Viktoriia V. Pakalnis Roman O. Iakovenko Dmitry S. Yufit Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems Beilstein Journal of Organic Chemistry acylketene azirine domino reaction furandione |
| title | Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems |
| title_full | Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems |
| title_fullStr | Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems |
| title_full_unstemmed | Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems |
| title_short | Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems |
| title_sort | domino reactions of 2h azirines with acylketenes from furan 2 3 diones competition between the formation of ortho fused and bridged heterocyclic systems |
| topic | acylketene azirine domino reaction furandione |
| url | https://doi.org/10.3762/bjoc.10.74 |
| work_keys_str_mv | AT alexanderfkhlebnikov dominoreactionsof2hazirineswithacylketenesfromfuran23dionescompetitionbetweentheformationoforthofusedandbridgedheterocyclicsystems AT mikhailsnovikov dominoreactionsof2hazirineswithacylketenesfromfuran23dionescompetitionbetweentheformationoforthofusedandbridgedheterocyclicsystems AT viktoriiavpakalnis dominoreactionsof2hazirineswithacylketenesfromfuran23dionescompetitionbetweentheformationoforthofusedandbridgedheterocyclicsystems AT romanoiakovenko dominoreactionsof2hazirineswithacylketenesfromfuran23dionescompetitionbetweentheformationoforthofusedandbridgedheterocyclicsystems AT dmitrysyufit dominoreactionsof2hazirineswithacylketenesfromfuran23dionescompetitionbetweentheformationoforthofusedandbridgedheterocyclicsystems |