Helvetica Chimica Acta Vol. 85(2002)
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5,6-Dihydro-2-{4-{[(4-methylphenyl)sulfonyl]oxy}phenyl}-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile
(27): Yield 66%. M.p. 1098. IR (KBr): 2320, 1660. 1H-NMR (300 MHz, (D6)DMSO): 2.42 (s, 3 H); 2.92 (t, 2 H);
3.90 (t, 2 H); 4.85( s, 2 H); 7.15 7.82 ( m, 8 arom. H). Anal. calc. for C19H17N3O5S (399.33): C 57.17, H 4.29,
N 10.52; found: C 57.10, H 4.19, N 10.57.
2-[4-(Benzoyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile (28): Yield 68%. M.p.
1
1538. IR (KBr): 2240, 1680. H-NMR (300 MHz, (D6)DMSO): 2.90 (t, 2 H); 3.91 (t, 2 H); 4.99 (s, 2 H); 6.81
7.42 (m, 9 arom. H). Anal. calc. for C19H15N3O4 (349.34): C 65.32, H 4.33, N 12.03; found: C 65.27, H 4.26,
N 12.00.
2-[4-(Benzyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile (29): Yield 76%. M.p.
1408. IR (KBr): 2240, 1680. 1H-NMR (300 MHz, (D6)DMSO): 2.90 (t, 2 H); 3.91 (t, 2 H); 4.84 (s, 2 H); 5.22
(s, 2 H); 7.20 7.35( m, 9 arom. H). Anal. calc. for C19H17N3O3 (335.36): C 68.05, H 5.11, N 12.53; found:
C 68.00, H 5.15, N 12.48.
5,6-Dihydro-2-{3-{[(4-methylphenyl)sulfonyl]oxy}phenyl}-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile
(30): Yield 60%. M.p. 2778. IR (KBr): 2260, 1690. 1H-NMR (300 MHz, (D6)DMSO): 2.39 (s, 3 H); 2.82 (t, 2 H);
4.12 (t, 2 H); 4.78 (s, 2 H); 7.05 7.45 ( m, 8 arom. H). Anal. calc. for C19H17N3O5S (399.33): C 57.18, H 4.29,
N 10.52; found: C 57.14, H 4.30, N 10.48.
2-[3-(Benzoyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile (31). Yield 65%. M.p.
1
2288. IR (KBr): 2260, 1698, 1665. H-NMR (300 MHz, (D6)DMSO): 2.82 (t, 2 H); 3.95( t, 2 H); 4.85( s, 2 H);
6.90 7.91 (m, 9 arom. H). Anal. calc. for C19H15N3O4 (349.34): C 65.32, H 4.33, N 12.03; found: C 65.27, H 4.35,
N 12.00.
2-[3-(Benzyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile (32): Yield 63%. M.p.
958. IR (KBr): 2100, 1660. 1H-NMR (300 MHz, (D6)DMSO): 2.85( t, 2 H); 3.91 (t, 2 H); 4.85( s, 2 H); 5.16
(s, 2 H); 7.10 7.45( m, 9 arom. H). Anal. calc. for C19H17N3O3 (335.36): C 68.05, H 5.11, N 12.53; found:
C 68.08, H 5.07, N 12.47.
2-(1H-Indol-3-ylmethyl)-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile (33): Yield 85%. M.p.
1
898. IR (KBr): 2350, 1685. H-NMR (300 MHz, (D6)DMSO): 2.82 (t, 2 H); 3.82 (t, 2 H); 4.40 4.70 (m, 4 H);
6.90 7.65( m, 5arom. H). Anal. calc. for C 15H14N4O2 (282.30): C 63.82, H 5.00, N 19.85; found: C 63.76, H 4.93,
N 19.88.
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