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...

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Autores principales: Bakulina, Olga, Ivanov, Alexander, Suslonov, Vitalii, Dar’in, Dmitry, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5530605/
https://www.ncbi.nlm.nih.gov/pubmed/28781707
http://dx.doi.org/10.3762/bjoc.13.138
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author Bakulina, Olga
Ivanov, Alexander
Suslonov, Vitalii
Dar’in, Dmitry
Krasavin, Mikhail
author_facet Bakulina, Olga
Ivanov, Alexander
Suslonov, Vitalii
Dar’in, Dmitry
Krasavin, Mikhail
author_sort Bakulina, Olga
collection PubMed
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.
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spelling pubmed-55306052017-08-04 A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline Bakulina, Olga Ivanov, Alexander Suslonov, Vitalii Dar’in, Dmitry Krasavin, Mikhail Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2017-07-18 /pmc/articles/PMC5530605/ /pubmed/28781707 http://dx.doi.org/10.3762/bjoc.13.138 Text en Copyright © 2017, Bakulina et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Bakulina, Olga
Ivanov, Alexander
Suslonov, Vitalii
Dar’in, Dmitry
Krasavin, Mikhail
A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline
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 Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5530605/
https://www.ncbi.nlm.nih.gov/pubmed/28781707
http://dx.doi.org/10.3762/bjoc.13.138
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