Cycloaddition of 3-Amino-5-chloro-2(1H)-pyrazinones and Olefins:  Ring Transformation into 3-Amino- or 6-Cyano-Substituted 2-Pyridinone Systems

• Published in: Journal of organic chemistry Vol. 61; no. 1; pp. 304 - 308
• Main Authors: Vandenberghe, Stef M, Buysens, Kris J, Meerpoel, Lieven, Loosen, Patrick K, Toppet, Suzanne M, Hoornaert, Georges J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.01.1996; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; AZADIENES; 2(1H)-PYRAZINONES; DIELS-ALDER REACTIONS; SCOPE

The cycloadducts formed from the Diels−Alder reaction of 3-amino-5-chloro-2(1H)-pyrazinones with methyl acrylate in toluene are subject to two alternative modes of ring transformation yielding either methyl 6-cyano-1,2-dihydro-2-oxo-4-pyridinecarboxylates, e.g. 12a,b (loss of amine substituent), or...