A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline
A series of 15 benzene-fused hexahydropyrrolo[1,2-b]isoquinolonic acids with substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli–Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine c...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.138 |
| _version_ | 1818919148045991936 |
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| author | Olga Bakulina Alexander Ivanov Vitalii Suslonov Dmitry Dar’in Mikhail Krasavin |
| author_facet | Olga Bakulina Alexander Ivanov Vitalii Suslonov Dmitry Dar’in Mikhail Krasavin |
| author_sort | Olga Bakulina |
| collection | DOAJ |
| description | A series of 15 benzene-fused hexahydropyrrolo[1,2-b]isoquinolonic acids with substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli–Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine component reaction allowed, for the first time, isolating a Mannich-type adduct between HPA and an imine component which has been postulated but never obtained in similar reactions. |
| first_indexed | 2024-12-20T01:01:15Z |
| format | Article |
| id | doaj.art-ff0411622d344a9ca4efe82f7d103bee |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T01:01:15Z |
| publishDate | 2017-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ff0411622d344a9ca4efe82f7d103bee2022-12-21T19:58:59ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-07-011311413142410.3762/bjoc.13.1381860-5397-13-138A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinolineOlga Bakulina0Alexander Ivanov1Vitalii Suslonov2Dmitry Dar’in3Mikhail Krasavin4Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, RussiaInstitute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, RussiaInstitute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, RussiaInstitute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, RussiaInstitute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, RussiaA series of 15 benzene-fused hexahydropyrrolo[1,2-b]isoquinolonic acids with substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli–Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine component reaction allowed, for the first time, isolating a Mannich-type adduct between HPA and an imine component which has been postulated but never obtained in similar reactions.https://doi.org/10.3762/bjoc.13.138Castagnoli–Cushman reactiondiastereoselectivityhomophthalic anhydrideindolenineslactam synthesismulticomponent reactions |
| spellingShingle | Olga Bakulina Alexander Ivanov Vitalii Suslonov Dmitry Dar’in Mikhail Krasavin A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline Beilstein Journal of Organic Chemistry Castagnoli–Cushman reaction diastereoselectivity homophthalic anhydride indolenines lactam synthesis multicomponent reactions |
| title | A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline |
| title_full | A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline |
| title_fullStr | A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline |
| title_full_unstemmed | A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline |
| title_short | A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline |
| title_sort | speedy route to sterically encumbered benzene fused derivatives of privileged naturally occurring hexahydropyrrolo 1 2 b isoquinoline |
| topic | Castagnoli–Cushman reaction diastereoselectivity homophthalic anhydride indolenines lactam synthesis multicomponent reactions |
| url | https://doi.org/10.3762/bjoc.13.138 |
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