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Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core

Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core

Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols wit...

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Главные авторы: Arutiunov, N. A., Арутюнов, Н. А., Shcherbakov, S. V., Щербаков, С. В., Shtal, D. A., Шталь, Д. А., Shcheglov, M. O., Щеглов, М. О., Tolstov, K. V., Толстов, К. В., Murashkina, D. I., Мурашкина, Д. И., Aksenov, N. A., Аксенов, Н. А., Aksenov, A. V., Аксенов, А. В.
Формат: Статья
Язык:English
Опубликовано: Elsevier Ltd 2025
Темы:
Acetylenes
Pyrimidine
Electrophilic cyclization
Heterocycles
Spiroannulation
Online-ссылка:https://dspace.ncfu.ru/handle/123456789/30656
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spelling ir-123456789-306562025-07-02T10:04:59Z Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core Arutiunov, N. A. Арутюнов, Н. А. Shcherbakov, S. V. Щербаков, С. В. Shtal, D. A. Шталь, Д. А. Shcheglov, M. O. Щеглов, М. О. Tolstov, K. V. Толстов, К. В. Murashkina, D. I. Мурашкина, Д. И. Aksenov, N. A. Аксенов, Н. А. Aksenov, A. V. Аксенов, А. В. Acetylenes Pyrimidine Electrophilic cyclization Heterocycles Spiroannulation Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine. Subsequently, an oxidation, palladium-catalyzed Sonogashira cross-coupling reaction and electrophilic spirocyclization, allowed to target product with good yields and simple synthetic protocols. 2025-07-02T10:03:21Z 2025-07-02T10:03:21Z 2025 Статья Arutiunov N.A., Shcherbakov S.V., Shtal D.A., Shcheglov M.O., Tolstov K.V., Murashkina D.I., Aksenov N.A., Aksenov A.V. Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core // Tetrahedron. - 2025. - 184. - art. no. 134791. - DOI: 10.1016/j.tet.2025.134791 https://dspace.ncfu.ru/handle/123456789/30656 en Tetrahedron application/pdf application/pdf Elsevier Ltd
institution СКФУ
collection Репозиторий
language English
topic Acetylenes
Pyrimidine
Electrophilic cyclization
Heterocycles
Spiroannulation
spellingShingle Acetylenes
Pyrimidine
Electrophilic cyclization
Heterocycles
Spiroannulation
Arutiunov, N. A.
Арутюнов, Н. А.
Shcherbakov, S. V.
Щербаков, С. В.
Shtal, D. A.
Шталь, Д. А.
Shcheglov, M. O.
Щеглов, М. О.
Tolstov, K. V.
Толстов, К. В.
Murashkina, D. I.
Мурашкина, Д. И.
Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
description Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine. Subsequently, an oxidation, palladium-catalyzed Sonogashira cross-coupling reaction and electrophilic spirocyclization, allowed to target product with good yields and simple synthetic protocols.
format Статья
author Arutiunov, N. A.
Арутюнов, Н. А.
Shcherbakov, S. V.
Щербаков, С. В.
Shtal, D. A.
Шталь, Д. А.
Shcheglov, M. O.
Щеглов, М. О.
Tolstov, K. V.
Толстов, К. В.
Murashkina, D. I.
Мурашкина, Д. И.
Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
author_facet Arutiunov, N. A.
Арутюнов, Н. А.
Shcherbakov, S. V.
Щербаков, С. В.
Shtal, D. A.
Шталь, Д. А.
Shcheglov, M. O.
Щеглов, М. О.
Tolstov, K. V.
Толстов, К. В.
Murashkina, D. I.
Мурашкина, Д. И.
Aksenov, N. A.
Аксенов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
author_sort Arutiunov, N. A.
title Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
title_short Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
title_full Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
title_fullStr Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
title_full_unstemmed Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
title_sort electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7′-cyclopenta[d]pyrimidin]-4-one core
publisher Elsevier Ltd
publishDate 2025
url https://dspace.ncfu.ru/handle/123456789/30656
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