Nachbargruppenbeteiligung bei der Dehydrierung cyclischer Amine vom Typ o-substituierter Anilinderivate / Neighbourgroup Participation with the Dehydrogenation of Cyclic Amines of the o-Substituted Aniline Type

Autor:	H. Möhrle, J. Mehrens
Rok vydání:	1998
Předmět:	Chemistry medicine.drug_class General Chemistry Medicinal chemistry Aminoketone chemistry.chemical_compound Aniline Nucleophile Lactam medicine Hemiaminal Organic chemistry Hydroxymethyl Dehydrogenation Amine gas treating
Zdroj:	Zeitschrift für Naturforschung B. 53:1369-1378
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-1998-1123
Popis:	The 2-Aminobenzylalcohols la - c produced with mercury-edta dehydrogenation the lactams 6a - c; the pipecoline 2b yielded the benzoxazine 3b indicating the participation of the nucleophilic hydroxymethyl group. The 2-aminobenzaldehydes showed a different behaviour in dependence on the ring size of the amine part: 7a, b led - via intermediate reaction of the hemiaminal 9 with the electrophilic formyl function - to the lactams 11a, b, while 7c gave rise to the aminoaldehyde 12 as major product and similarly the pipecoline 15 to the aminoketone 16. From 2′-(4-morpholinyl)-acetophenone (22) were received the lactam 31 and the aminoethanol 32, both by a twofold dehydrogenation.
Databáze:	OpenAIRE
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