492
A. V. Karnik, N. J. Malviya, A. M. Kulkarni, D. Jaimini and B. L. Jadhav
Vol. 43
120.42, 122.49, 122.68, 124.35, 126.54, 127.62, 129.07,
129.57(2C), 135.83, 138.89, 148.28, 151.97, 155.95, 160.92.
Anal. Calcd for C H N O S : % C,66.00; H, 4.00; N, 14.00; O,
This compound was obtained as light brown solid, mp 170-172
°C, ir (KBr) 1580, 1600, 1620, 2950,3005. pmr: (60 MHz
DMSO) δ 4.58 (t, 1H, C(2a)-H) 5.95 (dd, 1H, C(2)-H ), 5.15 (dd,
1H, C(2)-H ), 7.4-7.8 (m, 8H, Ar), 8.0 (d, 1H, Ar J= 4 Hz) 8.2 (d,
22 16
4 2
7.99; S, 8.00. Found % C, 65.72; H, 3.75; N, 13.78; O, 7.72; S, 7.78.
+
+
1H, C-14(H) Ar J=8.4 Hz.). ms: m/z 371(M ), 372(M+1) ,
11-Bromo-6-[2'-methoxyphenyl]-2,2a-dihydro-naphtho[2',1'-
5,6]pyrano[4,3-e] [1,2,4]triazolo [3,4-b][1,3,4]thiadiazine (4d).
+
373(M+2) .
Anal. Calcd. for C
H N OS : % C, 64.69; H, 3.50; N, 18.87;
20 13 5
This compound was obtained as brown solid, mp 160-161 °C,
ir (KBr) 1580, 1600, 1620, 2950,3005. pmr: (60 MHz DMSO)
O, 4.31; S, 8.63. Found % C, 64.42; H, 3.26; N, 18.60; O, 4.06; S,
8.36.
δ3.8 (s, 3H, 0CH ), 4.5 (t, 1H, C(2a)-H) 4.8 (dd, 1H, C(2)-H), 5.1
3
11-Bromo-6-Pyridin-3'-yl-2,2a-dihydro-naphtho[2',1'-5,6]-
pyrano[4,3-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (4j).
(dd, 1H, C(2)-H), 7.5-7.8 (m, 7H, Ar), 7.8 (d, 1H, C-12(H) Ar J=
4Hz) 8.10 (d, 1H, C-14(H) Ar J=8.4 Hz).
Anal. Calcd for C
16.70; N, 11.69; O, 6.68; S, 6.69. Found % C, 54.85; H, 2.90; Br,
16.44; N, 11.42; O, 6.42; S, 6.42.
H
BrN O S : % C, 55.12; H, 3.13; Br,
This compound was obtained as brown solid, mp 179-180 °C,
ir (KBr) 1580, 1600, 1620, 2950, 3005. pmr: (60 MHz DMSO) δ
4.55 (t, 1H, C(2a)-H) 5.05 (dd, 1H, C(2)-H), 5.30 (dd, 1H, C(2)-
H), 7.45-7.75 (m, 7H, Ar) 7.80 (d, 1H, C-12(H) Ar J= 4 Hz),
8.10(d, 1H, C-14(H) Ar J=8.4 Hz).
22 15
4 2
6-[4'-Chlorophenyl]-2,2a-dihydro-naphtho[2',1'-5,6]pyrano[4,3-
e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (4e).
Anal. Calcd. for C
H BrN OS : % C, 53.33; H, 2.66; Br,
20 12 5
This compound was obtained as yellow solid, mp 209-210 °C,
ir (KBr) 1580, 1600, 1620, 2950, 3005. pmr: (60 MHz DMSO) δ
4.8 (t, 1H, C(2a)-H) 5.0 (dd, 1H, C(2)-H), 5.2 (dd, 1H, C(2)-H),
7.2-7.8 (m, 8H, Ar) 7.9 (d, 1H, Ar J= 4Hz) 8.10 (d, 1H, C-14(H)
Ar J=8.4 Hz).
17.77; N, 15.55; O, 3.55; S, 7.11. Found % C, 53.10; H, 2.46; Br,
17.49; N, 15.30; O, 3.32; S, 6.90.
7-Bromo-naphtho [1,2-b]pyran-4-one (5b).
This compound was obtained as white solid, mp 154 ºC
-1
Anal. Calcd. for C
H ClN OS : % C, 62.38; H, 3.22; Cl,
(decomp), ir (KBr): C=C 1600, 1620,C=O 1660cm . pmr:
21 13 4
8.66; N, 13.86; O, 3.95; S,7.92. Found % C, 62.15; H, 3.01; Cl,
8.50; N, 13.61; O, 3.67; S, 7.65.
(60Mhz) (DMSO) δ 6.5(d, 1H, CH, J = 8hz) and 7.1-8.2 (m,6H,
Ar and CH).
Anal. Calcd. for C H BrO : % C, 56.76; H, 2.56; Br, 29.05.
Found % C, 56.40; H, 2.32; Br, 28.70.
13
7
2
11-Bromo-6-[4'-Chlorophenyl]-2,2a-dihydro-naphtho[2',1'-
5,6]pyrano[4,3-e][1,2,4]triazolo [3,4-b][1,3,4]thiadiazine (4f).
Acknowledgement.
This compound was obtained as yellow solid, mp 184-185 °C,
ir (KBr) 1580, 1600, 1620, 2950,3005. pmr: (60 MHz DMSO) δ
4.6 (t, 1H, C(2a)-H) 5.01 (dd, 1H, C(2)-H), 5.15 (dd, 1H, C(2)-
H), 7.4-7.8 (m, 7H, Ar) 7.94 (d, 1H, C-12(H) Ar J= 4Hz), 8.10 (d,
1H, C-14(H) Ar J=8.4 Hz).
We are thankful to Mr. R. R. Dalvi Vice-President and Mr. K.
T. Neurgaonkar Sr. Manger R. P. G. Life Sciences Pvt. Ltd. for
their help in recording Mass spectra of our compounds.
Anal. Calcd. for C
16.56; Cl, 7.25; N, 11.59; O, 3.31; S, 6.63; Found % C, 51.88; H,
2.22; Br, 16.31; Cl, 7.02; N, 11.34; O, 3.08; S, 6.36.
H BrClN OS : % C, 52.17; H, 2.48; Br,
21 12 4
REFERENCES AND NOTES
[1a] M. Alauddin and M. M. Smith, J. Pharm and Pharmacol., 14,
469 (1962); [b] M. Alauddin and M. M. Smith, J. Pharm. and
Pharmacol., 14, 325 (1962); [c] M. F. Sugrue and M. M. Smith, J. Pharm.
and Pharmacol., 16, 569 (1962).
[2] C. I. Turner, R. M. Williamson, P. Turner and M. S. Sherburn,
Chem. Comm., 1610 (2003).
[3] L. F. Tietze, K. M. Sommer, G. Schneider, P. Topolcsanyi, J.
Wolfling, P. Muller, M. Noltemeyer and H. Terlau, Synlett., 10, 1494
(2003).
6-[4'-Nitrophenyl]-2,2a-dihydro-naphtho[2',1'-5,6]pyrano[4,3-
e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (4g).
This compound was obtained as yellow solid mp 225-226 °C,
ir (KBr) 1580, 1600, 1620, 2950,3005. pmr: (DMSO) pmr: (60
MHz DMSO) δ 4.6 (t, 1H, C(2a)-H) 5.05 (dd, 1H, C(2)-H), 5.35
(dd, 1H, C(2)-H), 7.5-7.7 (m, 8H, Ar), 7.9 (d, 1H, Ar J= 4 Hz),
8.15 (d, 1H, C-14(H) Ar J=8.4 Hz).
Anal. Calcd. for C
16.87; O, 11.55; S,7.71;. Found % C, 60.46; H, 3.00; N, 16.62; O,
11.28; S, 7.48.
H N O S : % C, 60.72; H, 3.13; N,
[4] R. O. Clinton, A. J. Manson, F. W. Stonner, A. L. Beyeler, G.
O. Potts and A. Arnold, J. Am. Chem. Soc., 81, 1513 (1959).
[5] R. W. Kierstead, A. Faraone and A. Boris, J. Med. Chem., 10,
177 (1967).
[6] R. O. Clinton, A. J. Manson, F. W. Stonner, H. C. Neumann,
R. G. Chritiansen and R. L. Clarke, J. Am. Chem. Soc., 83, 1478 (1961).
[7] J. Abraham, D. P. Jindal and Harkishan Singh, Indian J.
Chem., 31B, 566 (1992).
[8] Anastasiou, P. Catsoulacus and K. Epitheor, Farmakol
Farmakokinet Int Ed, 6(3), 130 (1992); Chem. Abstr., 119, 72911w
(1993).
[9] Akherm, F. A. Lakhvich, B. B. Kuz’mitskii and S. F.
Gorbatenko, Chem. Abstr., 90, 104211u (1979).
21 13 5 3
11-Bromo-6-[4'-nitrophenyl]-2,2a-dihydro-naphtho[2',1'-5,6]-
pyrano[4,3-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (4h).
This compound was obtained as brown solid, mp 187-188 °C,
ir (KBr) 1580, 1600, 1620, 2950,3005. pmr: (60 MHz DMSO) δ
4.6 (t, 1H, C(2a)- H) 5.01 (dd, 1H, C(2)-H ), 5.15 (dd, 1H, C(2)-
H), 7.4-7.8 (m, 7H, Ar) 7.94 (d, 1H, C-12(H) Ar J= 4 Hz) 8.10
(d, 1H, C-14(H) Ar J=8.4 Hz).
Anal. Calcd. for C
H BrN O S : % C, 51.01; H, 2.43;
21 12 5 3
[10] G. P. Ellis, Heterocyclic Compounds, Chromenes,
Chromanones and Chromones, 31, 211, 335, 343 and 577 (1977).
[11a] H. S. Dong, K. Wei, Q. L. Wang and B. Quan J. Chinese
Chem. Soc., 47, 541 (2000); [b] X. P. Hui, L. M. Zhang, Z. Y. Zhang, Q.
W. and F. Wangb J. Chinese Chem. Soc., 47, 535 (2000).
Br,16.19; N, 14.17; O, 9.71; S,6.48. Found % C, 50.78; H, 2.18;
Br, 15.92; N, 13.90; O, 9.48; S, 6.24.
6-Pyridin-3'-yl-2,2a-dihydro-naphtho[2',1'-5,6]pyrano[4,3-
e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (4i).