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Synthesen mit Nitrilen, LVIII. Ein neuer Weg zu Isoxazolo[5,4‐ b ]pyridinen
Author(s) -
Junek Hans,
Thierrichter Burkhard,
Lukas Gerda
Publication year - 1980
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19801130341
Subject(s) - chemistry , malononitrile , medicinal chemistry , dimer , tetracyanoethylene , derivative (finance) , stereochemistry , organic chemistry , catalysis , financial economics , economics
Syntheses with Nitriles, LVIII. A New Route to Isoxazolo[5,4‐ b ]pyridines Reaction of dimeric malononitrile (2‐amino‐1‐propene‐1,1,3‐tricarbonitrile) ( 1 ) with benzo‐hydroximoyl chlorides in alkaline medium leads to substituted isoxazolo[5,4‐ b ]pyridines 6a – e . The isoxazole derivative 4a is an isolable intermediate. Condensation of the mixed dimer from malononitrile and methyl cyanoacetate (methyl 3‐amino‐2,4‐dicyanocrotonate) ( 3 ) with benzo‐hydroximoyl chlorides yields methyl 3‐amino‐3‐(5‐amino‐3‐aryl‐4‐isoxalyl)‐2‐cyanoacrylates ( 5a – c ). 6,7‐Dihydro‐6‐oxoisoxazolo[5,4‐ b ]pyridines 7a,c are obtained from 5a,c by elimination of alcohol.