790
A. H. Kategaonkar et al.
8-Methyltetrazolo[1,5-a]quinoline-4-carbonitrile
(3c, C11H7N5)
7-Ethoxytetrazolo[1,5-a]quinoline-4-carbonitrile
(3h, C12H9N5O)
ꢀ
ꢀ
Yield 87%; m.p.: 232–234 °C; IR (KBr): m = 3,084 (arom.
Yield 78%; m.p.: 298–300 °C; IR (KBr): m = 3,074 (arom.
C–H), 2,235 (C:N), 1,537 (tetrazole stretch), 1,467
C–H), 2,224 (C:N), 1,521 (tetrazole stretch), 1,478
(arom. C=C) cm-1
;
1H NMR (300 MHz, DMSO-d6):
(arom. C=C) cm-1 1H NMR (300 MHz, DMSO-d6):
;
d = 2.43 (s, 3H, Ar–CH3), 7.78 (d, 1H, J = 8.7 Hz, Ar–
H), 7.91 (s, 1H, Ar–H), 8.43 (d, 1H, J = 8.7 Hz, Ar–H),
9.16 (s, 1H, Ar–H) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 20.5, 97.4, 114.6, 116.1, 122.2, 129.8, 130.0, 136.3,
138.4, 144.1, 146.3 ppm; MS: m/z = 210.2 [M ? 1].
d = 1.35 (t, 3H, J = 6.9 Hz, Ar–OCH2–CH3), 4.34 (q, 2H,
J = 6.9 Hz, Ar–OCH2–CH3), 7.24–7.42 (m, 3H, Ar–H),
8.63 (s, 1H, Ar–H) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 14.6, 63.6, 106.2, 110.2, 116.1, 117.1, 118.2, 124.2,
138.8, 148.9, 153.8, 158.3 ppm; MS: m/z = 240.1
[M ? 1].
9-Methyltetrazolo[1,5-a]quinoline-4-carbonitrile
(3d, C11H7N5)
9-Ethyltetrazolo[1,5-a]quinoline-4-carbonitrile
(3i, C12H9N5)
ꢀ
Yield 74%; m.p.: 244–246 °C; IR (KBr): m = 3,097 (arom.
ꢀ
C–H), 2,239 (C:N), 1,528 (tetrazole stretch), 1,470
Yield 76%; m.p.: 178–180 °C; IR (KBr): m = 3,084 (arom.
(arom. C=C) cm-1
;
1H NMR (300 MHz, DMSO-d6):
C–H), 2,232 (C:N), 1,524 (tetrazole stretch), 1,465
d = 2.51 (s, 3H, Ar–CH3), 7.87 (s, 1H, Ar–H), 8.01 (d, 1H,
J = 8.7 Hz, Ar–H), 8.57 (d, 1H, J = 8.7 Hz, Ar–H), 9.04
(s, 1H, Ar–H) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 20.1, 97.3, 114.1, 116.7, 123.1, 129.4, 129.9, 136.8,
138.3, 144.1, 147.1 ppm; MS: m/z = 210.2 [M ? 1].
(arom. C=C) cm-1 1H NMR (300 MHz, DMSO-d6):
;
d = 1.36 (t, 3H, J = 6.9 Hz, Ar–CH2–CH3), 3.55 (q, 2H,
J = 6.9 Hz, Ar–CH2–CH3), 7.24 (t, 1H, J = 9.1 Hz, Ar–
H), 7.55 (d, 1H, J = 7.2 Hz, Ar–H), 8.77 (s, 1H, Ar–H)
ppm; 13C NMR (100 MHz, DMSO-d6): d = 14.8, 27.9,
106.2, 116.4, 118.6, 124.6, 129.7, 130.7, 138.3, 144.9,
155.9, 159.8 ppm; MS: m/z = 224.1 [M ? 1].
7-Methoxytetrazolo[1,5-a]quinoline-4-carbonitrile
(3e, C11H7N5O)
ꢀ
Yield 85%; m.p.: 200–202 °C; IR (KBr): m = 3,072 (arom.
Acknowledgments The authors would like to thank the Head of the
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada
University, Aurangabad for constant encouragement and providing
necessary facilities. AmHK also wishes to express his gratitude to the
University Grant Commission, New Delhi for providing the financial
support as a Rajiv Gandhi National Fellowship to carry out the
present work.
C–H), 2,240 (C:N), 1,551 (tetrazole stretch), 1,473
(arom. C = C) cm-1 1H NMR (300 MHz, DMSO-d6):
;
d = 3.94 (s, 3H, Ar–OMe), 7.69–7.76 (m, 2H, Ar–H), 8.55
(d, 1H, J = 9.0 Hz, Ar–H), 8.99 (s, 1H, Ar–H) ppm; 13C
NMR (100 MHz, DMSO-d6): d = 56.1, 97.5, 114.1, 116.7,
118.0, 123.9, 124.1, 125.8, 142.5, 145.0, 158.7 ppm; MS:
m/z = 226.2 [M ? 1].
References
8-Methoxytetrazolo[1,5-a]quinoline-4-carbonitrile
(3f, C11H7N5O)
1. El-Subbagh HI, Abu-Zaid SM, Mahran MA, Badria FA, Alofaid
AM (2000) J Med Chem 43:2915
2. Gupta R, Gupta AK, Paul S (2000) Ind J Chem 39B:847
3. Shekarchi M, Marvasti MB, Sharifzadeh M, Shafiee A (2005)
Iran J Pharm Res 1:33
ꢀ
Yield 76%; m.p.: 218–220 °C; IR (KBr): m = 3,100 (arom.
C–H), 2,236 (C:N), 1,530 (tetrazole stretch), 1,464
(arom. C=C) cm-1 1H NMR (300 MHz, DMSO-d6):
;
d = 3.85 (s, 3H, Ar–OMe), 7.57–7.69 (m, 2H, Ar–H), 8.48
(d, 1H, J = 8.1 Hz, Ar–H), 8.86 (s, 1H, Ar–H) ppm; 13C
NMR (100 MHz, DMSO-d6): d = 56.3, 97.4, 114.0, 116.4,
117.9, 122.8, 124.4, 126.3, 143.1, 145.6, 157.5 ppm; MS:
m/z = 226.2 [M ? 1].
4. Kumar P, Knaus EE (1994) Drug Des Discov 11:15
5. Shukla JS, Saxena S (1980) Indian Drugs 18:15
6. Ko OH, Kang HR, Yoo JC, Kim GS, Hong SS (1992) Yakhak
Hoechi 36:150
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9426725; (1995). Chem Abstr 122:214297
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34:557
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Perkin Trans 1:3166
10. Tennant G (1979) Comprehensive organic chemistry, vol 2.
Pergamon, Oxford, p 528
11. Srinivas KVNS, Bolla Reddy E, Das B (2002) Synlett 625
12. Lai G, Bhamare NK, Anderson WK (2001) Synlett 230
13. Janakiraman MN, Watenpaugh KD, Tomich PK, Chong KT,
Turner SR, Tommasi RA, Thaisrivongs S, Strohbach JW (1998)
Bioorg Med Chem Lett 8:1237
9-Methoxytetrazolo[1,5-a]quinoline-4-carbonitrile
(3g, C11H7N5O)
ꢀ
Yield 81%; m.p.: 206–208 °C; IR (KBr): m = 3,090 (arom.
C–H), 2,239 (C:N), 1,527 (tetrazole stretch), 1,472
(arom. C=C) cm-1 1H NMR (300 MHz, DMSO-d6):
;
d = 3.87 (s, 3H, Ar–OMe), 7.59 (s, 1H, Ar–H), 7.86 (d,
1H, J = 8.5 Hz, Ar–H), 8.54 (d, 1H, J = 8.1 Hz, Ar–H),
8.94 (s, 1H, Ar–H) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 56.1, 97.2, 114.1, 116.2, 118.7, 122.3, 124.6, 125.8,
144.6, 146.1, 158.3 ppm; MS: m/z = 226.2 [M ? 1].
14. Kamal A, Arifuddin M, Rao V (1998) Synth Commun 28:4507
15. Wittenberger SJ, Donner BG (1993) J Org Chem 58:4139
123