Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 619-631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02284
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Funding
- NSERC [29322]
- Higher Education Commission, Pakistan (IRSIP Program)
- Shastri Indo-Canadian Institute
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meta-Aminophenols are formed by treating 3-amino-2-chlorocyclohex-2-en-1-ones with DBU in MeCN at room temperature, and the chloro compounds are generated by using the halogenating agent BnNMe3·ICl2 in MeOH-CH2Cl2. The amino group must have two substituents, such as two aryl or one aryl and one alkyl group, which can be easily prepared from cyclohex-2-en-1-one and a primary or secondary amine.
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 center dot 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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