Formation of 3-Aminophenols from Cyclohexane-1,3-diones

doi:10.1021/acs.joc.0c02284

. 2021 Jan 1;86(1):619-631.

doi: 10.1021/acs.joc.0c02284. Epub 2020 Dec 4.

Formation of 3-Aminophenols from Cyclohexane-1,3-diones

Damian Szymor-Pietrzak¹, Muhammad N Khan², Anaïs Pagès³, Ajay Kumar⁴, Noah Depner¹, Derrick L J Clive⁵

Affiliations

¹ Undergraduate research participant, Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
² Visiting Scholar from the Chemistry Department, COMSATS University, Islamabad, Abbottabad Campus, Abbottabad 22010, Pakistan.
³ Research Intern from Ecole Nationale Supérieure d'Ingénieurs de Caen, Caen 14050, France.
⁴ Visiting Scholar from the Chemistry Department, Indian Institute of Technology (IIT), Gandhinagar 382355, India.
⁵ Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

PMID: 33274938
DOI: 10.1021/acs.joc.0c02284

Formation of 3-Aminophenols from Cyclohexane-1,3-diones

Damian Szymor-Pietrzak et al. J Org Chem. 2021.

. 2021 Jan 1;86(1):619-631.

doi: 10.1021/acs.joc.0c02284. Epub 2020 Dec 4.

Authors

Damian Szymor-Pietrzak¹, Muhammad N Khan², Anaïs Pagès³, Ajay Kumar⁴, Noah Depner¹, Derrick L J Clive⁵

Affiliations

¹ Undergraduate research participant, Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
² Visiting Scholar from the Chemistry Department, COMSATS University, Islamabad, Abbottabad Campus, Abbottabad 22010, Pakistan.
³ Research Intern from Ecole Nationale Supérieure d'Ingénieurs de Caen, Caen 14050, France.
⁴ Visiting Scholar from the Chemistry Department, Indian Institute of Technology (IIT), Gandhinagar 382355, India.
⁵ Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

PMID: 33274938
DOI: 10.1021/acs.joc.0c02284

Abstract

meta-Aminophenols are formed by the action of DBU on 3-amino-2-chlorocyclohex-2-en-1-ones at room temperature in MeCN. The chloro compounds are generated by treating 3-aminocyclohex-2-en-1-ones with the easily prepared halogenating agent BnNMe₃·ICl₂ in MeOH-CH₂Cl₂. The amino group must carry two substituents, either two aryl, one aryl and one alkyl, or two alkyl groups; 3-aminocyclohex-2-en-1-ones of this type are readily made from cyclohex-2-en-1-one and a primary or secondary amine.

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Formation of 3-Aminophenols from Cyclohexane-1,3-diones

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Formation of 3-Aminophenols from Cyclohexane-1,3-diones

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