J. Org. Chem. 1983, 48, 3564-3566
3564
Table 111. Yields, Boiling Points, and Spectroscopic Data of Compounds 9 a , b compd
yield, %
bp, “Clmbar (lit. bp)
9a
82 85 79 71 80 78
8017 7713 7412 106/1013 971180 (44-46/15)12 115/1013
9b 9c
9d 9e
9f
a All compounds displayed a broad IR absorption between 3350 and 3250 cm-l (film). ‘H NMR data (6 ) for 9a: 1.33 (br s, 1, NH), 2.38 (s, 3, CH,N), 4.08 (d, 1,J = 7 Hz, CHN), 5.0-5.4 (m, 2, H,C=), 5.7-6.3 (m, 1, HC=), 7.3 (“s”, 5, C,H,). For 9b: 1.27 (br s, 1 , NH), 1.6-1.7 (m, 3, CH,), 2.32 (s, 3, CH,N), 3.9-4.1 (m, 1 , CHN), 5.5-5.8 (m, 2, 2CH=), 7.3 (“s”, 5, C,H,). For 9c: 1.30 (br s, 1, NH), 1.50 (s, 3, CH,), 2.25 (s, 3, CH,N), 5.0-5.4 (m, 2, CH2=), 5.8-6.3 (m, 1, CH=), 7.27.6 (m, 5, C,H,). For 9d: 1.00 (br s, 1, NH), 1.10 (d, 3, J = 6.5 Hz, CH,C), 1.68 (“d”, 3, J = 5 Hz, CH,C< ), 2.33 (s, 3, CH,N), 2.8-3.3 (m, 1, CHN), 5.0-5.6 (m, 2, 2HC=). For 9e: 0.93 (br s, 1, NH), 1.3-2.2 (m, 6, (CH2),), 2.43 (s, 3, CH,N), 2.9-3.1 (m, 1, CHN), 5.75 (‘Is”, 2, 2HC=). For 9f: 1.00 (br s, 1, NH), 1.60 (d, 3, J = 5 Hz, CH,CH), 1.65 (s, 3, CH,C
