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^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

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.).

Original language	English
Pages (from-to)	4915-4925
Number of pages	11
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	21
DOIs	https://doi.org/10.1002/adsc.202100779
Publication status	Published - 2021 Nov 9

Keywords

3-bromopropenals
One-pot synthesis
anilines
dimethyl sulfoxide
α-bromo enaminones

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202100779

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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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journal = "Advanced Synthesis and Catalysis",

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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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U2 - 10.1002/adsc.202100779

DO - 10.1002/adsc.202100779

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 21

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 2087061: Experimental Crystal Structure Determination

CCDC 2087058: Experimental Crystal Structure Determination

CCDC 2087059: Experimental Crystal Structure Determination

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

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 2087061: Experimental Crystal Structure Determination

CCDC 2087058: Experimental Crystal Structure Determination

CCDC 2087059: Experimental Crystal Structure Determination

Cite this