Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9: Chemistry of aminophenols

Xinglong Xing; Jinlong Wu; Wei Min Dai

doi:10.1016/j.tet.2006.09.012

Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9: Chemistry of aminophenols

Xinglong Xing, Jinlong Wu, Wei Min Dai^*

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

The aza-Diels-Alder reactions of two 2-aminophenols in combination with six substituted benzaldehydes and two electron-rich cyclic alkenes were investigated under controlled microwave heating. The reactions were carried out in the presence of a catalytic amount of CF₃CO₂H in MeCN at 60 °C for 15 min, affording highly functionalized 8-hydroxy-1,2,3,4-tetrahydroquinolines in 39-59% isolated yields and in 36:64-16:84 diastereomer ratios in favor of the trans isomers. The microwave-heated three-component aza-Diels-Alder reactions completed in significantly reduced reaction time to give the same level of chemical yield and diastereomer ratio obtained from the room temperature reaction.

Original language	English
Pages (from-to)	11200-11206
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2006.09.012
Publication status	Published - 27 Nov 2006
Externally published	Yes

Keywords

2-Aminophenols
Aza-Diels-Alder cycloaddition
Microwave
Tetrahydroquinolines

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10.1016/j.tet.2006.09.012

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@article{a1b1842b44a446e893ecc5237321bf1b,

title = "Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9: Chemistry of aminophenols",

abstract = "The aza-Diels-Alder reactions of two 2-aminophenols in combination with six substituted benzaldehydes and two electron-rich cyclic alkenes were investigated under controlled microwave heating. The reactions were carried out in the presence of a catalytic amount of CF3CO2H in MeCN at 60 °C for 15 min, affording highly functionalized 8-hydroxy-1,2,3,4-tetrahydroquinolines in 39-59\% isolated yields and in 36:64-16:84 diastereomer ratios in favor of the trans isomers. The microwave-heated three-component aza-Diels-Alder reactions completed in significantly reduced reaction time to give the same level of chemical yield and diastereomer ratio obtained from the room temperature reaction.",

keywords = "2-Aminophenols, Aza-Diels-Alder cycloaddition, Microwave, Tetrahydroquinolines",

author = "Xinglong Xing and Jinlong Wu and Dai, \{Wei Min\}",

year = "2006",

month = nov,

day = "27",

doi = "10.1016/j.tet.2006.09.012",

language = "English",

volume = "62",

pages = "11200--11206",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "48",

}

Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9: Chemistry of aminophenols. / Xing, Xinglong; Wu, Jinlong; Dai, Wei Min.
In: Tetrahedron, Vol. 62, No. 48, 27.11.2006, p. 11200-11206.

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

TY - JOUR

T1 - Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9

T2 - Chemistry of aminophenols

AU - Xing, Xinglong

AU - Wu, Jinlong

AU - Dai, Wei Min

PY - 2006/11/27

Y1 - 2006/11/27

N2 - The aza-Diels-Alder reactions of two 2-aminophenols in combination with six substituted benzaldehydes and two electron-rich cyclic alkenes were investigated under controlled microwave heating. The reactions were carried out in the presence of a catalytic amount of CF3CO2H in MeCN at 60 °C for 15 min, affording highly functionalized 8-hydroxy-1,2,3,4-tetrahydroquinolines in 39-59% isolated yields and in 36:64-16:84 diastereomer ratios in favor of the trans isomers. The microwave-heated three-component aza-Diels-Alder reactions completed in significantly reduced reaction time to give the same level of chemical yield and diastereomer ratio obtained from the room temperature reaction.

AB - The aza-Diels-Alder reactions of two 2-aminophenols in combination with six substituted benzaldehydes and two electron-rich cyclic alkenes were investigated under controlled microwave heating. The reactions were carried out in the presence of a catalytic amount of CF3CO2H in MeCN at 60 °C for 15 min, affording highly functionalized 8-hydroxy-1,2,3,4-tetrahydroquinolines in 39-59% isolated yields and in 36:64-16:84 diastereomer ratios in favor of the trans isomers. The microwave-heated three-component aza-Diels-Alder reactions completed in significantly reduced reaction time to give the same level of chemical yield and diastereomer ratio obtained from the room temperature reaction.

KW - 2-Aminophenols

KW - Aza-Diels-Alder cycloaddition

KW - Microwave

KW - Tetrahydroquinolines

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000241967600020

UR - https://openalex.org/W2950239778

UR - https://www.scopus.com/pages/publications/33750123139

U2 - 10.1016/j.tet.2006.09.012

DO - 10.1016/j.tet.2006.09.012

M3 - Journal Article

SN - 0040-4020

VL - 62

SP - 11200

EP - 11206

JO - Tetrahedron

JF - Tetrahedron

IS - 48