Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones

Hai Huang; Guangke He; Guohao Zhu; Xiaolin Zhu; Shineng Qiu; Hongjun Zhu

doi:10.1021/acs.joc.5b00071

Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones

Hai Huang
, Guangke He
, Guohao Zhu
, Xiaolin Zhu
, Shineng Qiu
, Hongjun Zhu

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

42 Scopus citations

Abstract

A mild and efficient methodology involving Pd(PPh₃)₄-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl₂ or CuBr₂ for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.

Original language	English (US)
Pages (from-to)	3480-3487
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	80
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.5b00071
State	Published - Apr 3 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.5b00071

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title = "Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones",

abstract = "A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.",

author = "Hai Huang and Guangke He and Guohao Zhu and Xiaolin Zhu and Shineng Qiu and Hongjun Zhu",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.joc.5b00071",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - Palladium-catalyzed intramolecular cyclization of ynamides

T2 - Synthesis of 4-halo-oxazolones

AU - Huang, Hai

AU - He, Guangke

AU - Zhu, Guohao

AU - Zhu, Xiaolin

AU - Qiu, Shineng

AU - Zhu, Hongjun

PY - 2015/4/3

Y1 - 2015/4/3

N2 - A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.

AB - A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.

UR - https://www.scopus.com/pages/publications/84926484323

UR - https://www.scopus.com/pages/publications/84926484323#tab=citedBy

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SP - 3480

EP - 3487

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones

Abstract

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