Tetrahedron p. 3047 - 3051 (1980)
Update date:2022-08-05
Topics:
Shabana, R.
Rasmussen, J. B.
Olesen, S. O.
Lawesson, S.-O.
Imines, formed from cyclohexanone and primary aromatic and aliphatic amines, were reacted with β-propiolactone, acrylic, crotonic, and methacrylic acids to give as main products bicyclic lactams, 3,4,5,6,7,8-hexahydro-2-quinolinone, 2, and enaminones, 2,3,5,6,7,8-hexahydro-4-quinolinone, 3.The enaminones 3 and a series of noncyclic enaminones 11 were reacted with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 9, a new thiation reagent, giving the corresponding enamino-thiones 10 and 12, respectively.Compound 2a was also reacted with 9 giving N-phenyl- 3,4,5,6,7,8-hexahydro-2-quinolinthione, 13a. 360 MHz (1)H NMR and 90.25 MHz (13)C NMR data are reported for the compounds 2a, 3a and 10a.
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