A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones

Sundaram Suresh; Prakash Bhimrao Patil; Pao Hsing Yu; Chia Chi Fang; Yin Zhi Weng; Veerababurao Kavala; Ching Fa Yao

doi:10.1002/adsc.202100779

A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones

Sundaram Suresh, Prakash Bhimrao Patil, Pao Hsing Yu, Chia Chi Fang, Yin Zhi Weng, Veerababurao Kavala, Ching Fa Yao^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

5 引文斯高帕斯（Scopus）

摘要

A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H₂O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives. (Figure presented.).

原文	英語
頁（從 - 到）	4915-4925
頁數	11
期刊	Advanced Synthesis and Catalysis
卷	363
發行號	21
DOIs	https://doi.org/10.1002/adsc.202100779
出版狀態	已發佈 - 2021 11月 9

ASJC Scopus subject areas

催化
有機化學

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10.1002/adsc.202100779

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Link to publication in Scopus

CCDC 2087061: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Bhimrao Patil, P. (Contributor), Yu, P. (Contributor), Fang, C. (Contributor), Weng, Y. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc281rkn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc281rkn&sid=DataCite
資料集: Dataset
CCDC 2087058: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Bhimrao Patil, P. (Contributor), Yu, P. (Contributor), Fang, C. (Contributor), Weng, Y. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc281rgk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc281rgk&sid=DataCite
資料集: Dataset
CCDC 2087059: Experimental Crystal Structure Determination
Suresh, S. (Contributor), Bhimrao Patil, P. (Contributor), Yu, P. (Contributor), Fang, C. (Contributor), Weng, Y. (Contributor), Kavala, V. (Contributor) & Yao, C. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc281rhl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc281rhl&sid=DataCite
資料集: Dataset

引用此

@article{a6c146a01a7b4f2dba7257193dec95bc,

title = "A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones",

abstract = "A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives. (Figure presented.).",

keywords = "3-bromopropenals, One-pot synthesis, anilines, dimethyl sulfoxide, α-bromo enaminones",

author = "Sundaram Suresh and {Bhimrao Patil}, Prakash and Yu, {Pao Hsing} and Fang, {Chia Chi} and Weng, {Yin Zhi} and Veerababurao Kavala and Yao, {Ching Fa}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = nov,

day = "9",

doi = "10.1002/adsc.202100779",

language = "English",

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T1 - A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones

AU - Suresh, Sundaram

AU - Bhimrao Patil, Prakash

AU - Yu, Pao Hsing

AU - Fang, Chia Chi

AU - Weng, Yin Zhi

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2021/11/9

Y1 - 2021/11/9

N2 - A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives. (Figure presented.).

AB - A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives. (Figure presented.).

KW - 3-bromopropenals

KW - One-pot synthesis

KW - anilines

KW - dimethyl sulfoxide

KW - α-bromo enaminones

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ER -

A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 2087061: Experimental Crystal Structure Determination

CCDC 2087058: Experimental Crystal Structure Determination

CCDC 2087059: Experimental Crystal Structure Determination

引用此