Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates
Тип публикации: Journal Article
Дата публикации: 2003-03-28
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
12713344
Organic Chemistry
Краткое описание
The first palladium-catalyzed ring-expansion reaction of 2-vinylpyrrolidines with aryl isocyanates to form seven-membered ring heterocycles is described. This regioselective reaction requires 5 mol % of Pd(2)(dba)(3).CHCl(3) and 10 mol % of dppp at 40-60 degrees C in THF and results in the formation of 1,3-diazepin-2-ones in good isolated yields. When Pd(OAc)(2) and PPh(3) were utilized in the reaction, an intramolecular hydrogen migration occurs resulting in the formation of conjugated diene derivatives of urea.
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Zhou H., Alper H. Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates // Journal of Organic Chemistry. 2003. Vol. 68. No. 9. pp. 3439-3445.
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Zhou H., Alper H. Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates // Journal of Organic Chemistry. 2003. Vol. 68. No. 9. pp. 3439-3445.
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TY - JOUR
DO - 10.1021/jo020526x
UR - https://doi.org/10.1021/jo020526x
TI - Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates
T2 - Journal of Organic Chemistry
AU - Zhou, Hai-Bing
AU - Alper, Howard
PY - 2003
DA - 2003/03/28
PB - American Chemical Society (ACS)
SP - 3439-3445
IS - 9
VL - 68
PMID - 12713344
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2003_Zhou,
author = {Hai-Bing Zhou and Howard Alper},
title = {Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo020526x},
number = {9},
pages = {3439--3445},
doi = {10.1021/jo020526x}
}
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MLA
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Zhou, Hai-Bing, and Howard Alper. “Synthesis of Seven-Membered Ring Diazepin-2-ones via Palladium-Catalyzed Highly Regioselective Cyclization of 2-Vinylpyrrolidines with Aryl Isocyanates.” Journal of Organic Chemistry, vol. 68, no. 9, Mar. 2003, pp. 3439-3445. https://doi.org/10.1021/jo020526x.
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