Tetrahedron p. 12529 - 12540 (1996)
Update date:2022-08-03
Topics:
Dubois, Kristof J.
Fannes, Christine C.
Toppet, Suzanne M.
Hoornaert, Georges J.
By selective reaction of the chlorimine function in the adducts 2 from 3,5-dichloro-2H-1,4-oxazin-2-ones and double bond systems, a series of 6-substituted 2-oxa-5-azabicyclo[2.2.2]oct-5-en-3-ones 3 could be generated. Lactone cleavage of the latter with alcohols or amines yielded variously substituted 4,5-dihydro-5-hydroxy-2-pyridinecarboxylic acid derivatives which were dehydrated to afford the corresponding pyridine systems. Some 6-amino substituted 2-pyridinecarboxamides could be obtained in a one step procedure by reacting 2 with Me3Al/amine.
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Doi:10.1016/S0960-894X(97)00350-8
(1997)Doi:10.1016/0040-4039(96)01719-4
(1996)Doi:10.1021/jo00838a038
(1969)Doi:10.1080/07328309608005699
(1996)Doi:10.1039/C8NJ04223C
(2019)Doi:10.1039/CT8875100040
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