Chemical and Pharmaceutical Bulletin p. 243 - 248 (1997)
Update date:2022-08-04
Topics: Quinones Cycloaddition Reactions α,β-Unsaturated Carbonyl Compounds Styrenes
Koike, Takeshi
Tanabe, Mituharu
Takeuchi, Naoki
Tobinaga, Seisho
Methyl 5-(N,N-dimethylamino)-2,4-pentadienoate (tert-aminodienylester 1) was synthesized by condensation of methyl crotonate (2) with N,N,N',N'- tetramethylenediamine (3). The reactivity of 1 was investigated with methyl propiolate (4), dimethyl 2-butynedionate (5), dimethyl maleate (6), dimethyl fumarate (7), 2-buten-4-olide (8), 2-cyclohexenone (9), styrene (10), trans- β-nitrostyrene (11), 1,4-benzoquinone (19), methyl 1,4-naphthoquinone-5- carboxylate (21), 1,4-naphthoquinone (24), juglone (26), 5-methoxy-1,4- naphthoquinone (28), naphthazarin (31), and naphthazarin dimethyl ether (33). In addition, 5-(N,N-dimethylamino)-2,4-pentadienenitrile (tert-aminodienyl- nitrile 37) was synthesized by condensation of crotononitrile (36) with 3. The reactivity of 37 was investigated with dimethyl 2-butynedionate (5), and 2-cyclohexenone (9).
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