Standard

DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study. / Филиппов, Илья Павлович; Захаров, Тимофей Николаевич; Гришин, Александр Валерьевич; Хлебников, Александр Феодосиевич; Новиков, Михаил Сергеевич; Ростовский, Николай Витальевич.

In: The Journal of organic chemistry, Vol. 89, No. 21, 04.10.2024, p. 15404–15413.

Research output: Contribution to journal › Article › peer-review

Harvard

Филиппов, ИП, Захаров, ТН, Гришин, АВ, Хлебников, АФ, Новиков, МС & Ростовский, НВ 2024, 'DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study', The Journal of organic chemistry, vol. 89, no. 21, pp. 15404–15413. https://doi.org/10.1021/acs.joc.4c00647

APA

Филиппов, И. П., Захаров, Т. Н., Гришин, А. В., Хлебников, А. Ф., Новиков, М. С., & Ростовский, Н. В. (2024). DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study. The Journal of organic chemistry, 89(21), 15404–15413. https://doi.org/10.1021/acs.joc.4c00647

Vancouver

Филиппов ИП, Захаров ТН, Гришин АВ, Хлебников АФ, Новиков МС, Ростовский НВ. DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study. The Journal of organic chemistry. 2024 Oct 4;89(21):15404–15413. https://doi.org/10.1021/acs.joc.4c00647

Author

Филиппов, Илья Павлович ; Захаров, Тимофей Николаевич ; Гришин, Александр Валерьевич ; Хлебников, Александр Феодосиевич ; Новиков, Михаил Сергеевич ; Ростовский, Николай Витальевич. / DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study. In: The Journal of organic chemistry. 2024 ; Vol. 89, No. 21. pp. 15404–15413.

BibTeX

@article{2f07a0c3bcd64427bb95e1e616a7669c,
title = "DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study",
abstract = "1,1-Di(alkoxycarbonyl)-4-cyclopentyl-2-azabuta-1,3-dienes react with DBU to form two types of heterocyclic products: 1H-cyclopenta[c]pyrid-1-ones and 3-hydroxy-1H-pyrroles. These previously unobserved transformations proceed through the formation of 1-azapentadienyl anion which undergoes 1,6-shift of the alkoxycarbonyl group to the cyclopentyl moiety followed by 1,6-cyclization to form the cyclopentapyridone (path a) and 1,5-cyclization accompanied by 1,3-shift of the methoxy group followed by dialkyl carbonate elimination to afford the hydroxypyrrole (path b). The mechanisms of the reactions were studied using DFT calculations. Pyridones can be synthesized in one pot in three steps via Rh(II)-catalyzed isomerization of 4-cyclopentylisoxazoles to 2H-azirines and their subsequent reaction with diazomalonic esters, followed by heating of the resulting 2-azabuta-1,3-dienes with DBU.",
author = "Филиппов, {Илья Павлович} and Захаров, {Тимофей Николаевич} and Гришин, {Александр Валерьевич} and Хлебников, {Александр Феодосиевич} and Новиков, {Михаил Сергеевич} and Ростовский, {Николай Витальевич}",
year = "2024",
month = oct,
day = "4",
doi = "10.1021/acs.joc.4c00647",
language = "English",
volume = "89",
pages = "15404–15413",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "21",

}

RIS

TY - JOUR

T1 - DBU-Promoted Cyclizations of Cyclopentyl-Substituted Oxazapolyenes to Cyclopentapyridones and Hydroxypyrroles: Experimental and DFT Study

AU - Филиппов, Илья Павлович

AU - Захаров, Тимофей Николаевич

AU - Гришин, Александр Валерьевич

AU - Хлебников, Александр Феодосиевич

AU - Новиков, Михаил Сергеевич

AU - Ростовский, Николай Витальевич

PY - 2024/10/4

Y1 - 2024/10/4

N2 - 1,1-Di(alkoxycarbonyl)-4-cyclopentyl-2-azabuta-1,3-dienes react with DBU to form two types of heterocyclic products: 1H-cyclopenta[c]pyrid-1-ones and 3-hydroxy-1H-pyrroles. These previously unobserved transformations proceed through the formation of 1-azapentadienyl anion which undergoes 1,6-shift of the alkoxycarbonyl group to the cyclopentyl moiety followed by 1,6-cyclization to form the cyclopentapyridone (path a) and 1,5-cyclization accompanied by 1,3-shift of the methoxy group followed by dialkyl carbonate elimination to afford the hydroxypyrrole (path b). The mechanisms of the reactions were studied using DFT calculations. Pyridones can be synthesized in one pot in three steps via Rh(II)-catalyzed isomerization of 4-cyclopentylisoxazoles to 2H-azirines and their subsequent reaction with diazomalonic esters, followed by heating of the resulting 2-azabuta-1,3-dienes with DBU.

AB - 1,1-Di(alkoxycarbonyl)-4-cyclopentyl-2-azabuta-1,3-dienes react with DBU to form two types of heterocyclic products: 1H-cyclopenta[c]pyrid-1-ones and 3-hydroxy-1H-pyrroles. These previously unobserved transformations proceed through the formation of 1-azapentadienyl anion which undergoes 1,6-shift of the alkoxycarbonyl group to the cyclopentyl moiety followed by 1,6-cyclization to form the cyclopentapyridone (path a) and 1,5-cyclization accompanied by 1,3-shift of the methoxy group followed by dialkyl carbonate elimination to afford the hydroxypyrrole (path b). The mechanisms of the reactions were studied using DFT calculations. Pyridones can be synthesized in one pot in three steps via Rh(II)-catalyzed isomerization of 4-cyclopentylisoxazoles to 2H-azirines and their subsequent reaction with diazomalonic esters, followed by heating of the resulting 2-azabuta-1,3-dienes with DBU.

U2 - 10.1021/acs.joc.4c00647

DO - 10.1021/acs.joc.4c00647

M3 - Article

VL - 89

SP - 15404

EP - 15413

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -

ID: 126734172