PATIL ET AL.
| 7
(
100 MHz, DMSO-d
32.69, 140.97, 146.19; MS (EI): m/z calcd. for [C
Found: 203.
6
): δ 10.88, 23.39, 46.80, 100.30, 101.76, 128.73,
Ar-H), 7.43 (d, Ar-2H), 7.56 (m, Ar-5H), 7.77 (d, J = 7.8 Hz, Ar-H), 7.92
1
3
1
9
H
10
N
6
+H]: 203.1.
(d, J = 5.1 Hz, Ar-H), 7.94 (s, Ar-H), 9.92 (s, Ar-H); C NMR (100 MHz,
DMSO-d ): δ 48.23, 101.06, 102.21, 110.07, 118.47, 127.58, 128.25,
29.03, 130.05, 133.35, 133.51, 133.81, 137.22, 137.93, 141.12,
6
1
7
-(Ethyl 4-butanoate)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine
8d)
White solid, yield: 85%, m.p. 138–141°C. IR (film) υ: 1713, 1630, 1486,
13 7
143.96, 146.30; MS (EI): m/z calcd. for [C20H N +H]: 352.1. Found:
(
351.9.
−1 1
1
410 cm ; H NMR (400 MHz, DMSO-d
.15–2.08 (m, ─CH ─CH ), 2.30 (t, J = 7.3 Hz, ─CO─CH
─CH ), 4.43 (t, J = 6.8 Hz, N─CH ─CH
J = 3.4 Hz, Ar-H), 7.77 (d, J = 3.4 Hz, Ar-H), 9.89 (s, Ar-H); C NMR
100 MHz, DMSO-d ): δ 13.95, 25.45, 30.53, 44.51, 59.86, 100.54,
01.89, 128.67, 132.77, 141.03, 146.18, 172.01; m/z calcd. for
+H]: 275.12. Found: 275.
6
): δ 1.12 (t, J = 7.1 Hz, CH
), 3.99 (q,
), 7.09 (d,
3
),
4.1.8
|
General procedure for the preparation of
2
2
2
2
compounds 8j–l
J = 7.1 Hz, ─OCH
2
3
2
2
13
To a mixture of 4-chloropyrrolo[2,3-d]pyrimidine (12 mmol) and
appropriate sulfonyl chloride (15 mmol) in acetone (10 mL) was added
a solution of aqueous sodium hydroxide (50%) (12 mmol). The reaction
mixture was monitored by TLC. After completion of the reaction,
mixture was precipitated then filtered, washed with mixture of
acetone/water 1:1 (5 mL), and dried under vacuum to afford
compounds 8j–l (70–75%).
(
6
1
12 14 6 2
[C H N O
7
-(3-Butene)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine (8e)
White solid, yield: 82%, m.p. 140–142°C. IR (film) υ: 3107, 3054, 1637,
−
1 1
1
534, 1489 cm ; H NMR (400 MHz, DMSO-d
CH ), 4.96 (m, N─CH
─CHCH ), 4.45 (t, J = 7.0 Hz, CHCH
.82–5.72 (m, ─CH ─CHCH ), 7.04 (d, J = 3.4 Hz, Ar-H), 7.74 (d,
J = 3.4 Hz, Ar-H), 9.83(s, Ar-H); CNMR(100 MHz, DMSO-d
6
): δ 2.60 (q, J = 6.8 Hz,
2
2
2
2
─CH ),
2
7-(Methylsulfonyl)pyrrolo[3,2-e]tetrazolo[1,5-c]-pyrimidine (8j)
Brown color solid, yield: 75%, m.p. 156–158°C. IR (film) υ: 3120, 2966,
−1 1
5
2
2
1
3
6
):δ34.45,
4.79, 100.54, 101.97, 117.70, 129.01, 132.84, 134.76, 141.15,
46.38; MS (EI): m/z calcd. for [C10 +H]: 215.0. Found: 214.7.
1353, 1262 cm ; H NMR (400 MHz, DMSO-d
6 3
): δ 3.98 (s, N─CH ),
4
1
7.05 (d, J = 3.4 Hz, Ar-H), 7.73 (d, J = 3.4 Hz, Ar-H), 9.88 (s, Ar-H) ppm,
1
3
H N
10 6
C NMR (100 MHz, DMSO-d
32.81, 141.28, 146.22; MS (EI): m/z calcd. for [C
239.0. Found: 238.9.
6
): δ 38.19, 100.28, 101.80, 129.68,
1
7 6 6 2
H N O S+H]:
7
-(Benzyl)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine (8f)
Brown solid, yield: 86%, m.p. 175–177°C. IR (film) υ: 3127, 3054, 1633,
−
1 1
1
534, 1513 cm ; H NMR (400 MHz, DMSO-d
6
): δ 5.63 (s, N─CH
2
),
7-(Phenylsulfonyl)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine (8k)
Brown color solid, yield: 72%, m.p. 169–172°C. IR (film) υ: 3120, 2966,
−1 1
7
.12 (d, J = 3.2 Hz, Ar-H), 7.25–7.35 (m, Ar-5H), 7.85 (d, J = 3.4 Hz, Ar-
1
3
H), 9.90 (s, Ar-H); C NMR (100 MHz, DMSO-d
6
): δ 48.55, 100.85,
02.04, 127.30, 127.66, 128.57, 128.82, 133.10, 137.21, 140.97,
46.20; MS (EI): m/z calcd. for [C13 +H]: 251.1. Found: 251.
1557, 1353, 1262 cm
6
; H NMR (400 MHz, DMSO-d ): δ 7.40 (d,
1
1
J = 3.7 Hz, Ar-H), 7.69 (t, J = 7.8 Hz, Ar-2H), 7.80 (t, J = 7.6 Hz, Ar-H),
1
3
H
10
N
6
8.20 (m, Ar-H), 10.05 (s, Ar-H) ppm; C NMR (100 MHz, DMSO-d
6
): δ
1
04.64, 106.64, 127.07, 128.80, 129.96, 135.48, 135.64, 136.80,
7
-(4-Methylbenzyl)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine (8g)
8 6 2
140.64, 145.88; MS (EI): m/z calcd. for [C12H N O S+H]: 301.04.
Yellow solid, yield: 86%, m.p. 182–184°C. IR (film) υ: 3108, 3055, 1637,
Found: 301.
−
1 1
1
486, 1260 cm ; H NMR (400 MHz, DMSO-d
N─CH ), 7.12 (m, Ar-3H), 7.20 (d, J = 8.0 Hz, Ar-2H), 7.83 (d, J = 3.4 Hz,
Ar-H), 9.90 (s, Ar-H); C NMR (100 MHz, DMSO-d
6 3
): δ 2.24 (s, CH ), 5.57 (s,
2
7-[(4-Methylphenyl)sulfonyl]pyrrolo[3,2-e]tetrazolo[1,5-c]-
pyrimidine (8l)
13
6
): δ 20.57, 48.34,
00.80, 102.02, 127.38, 128.78, 129.11, 133.09, 134.23, 136.98, 140.94,
46.21; MS (EI): m/z calcd. for [C14 +H]: 265.0. Found: 264.8.
1
1
Dark brown color solid, yield: 70%, m.p. 150–152°C. IR (film) υ: 3120,
−1 1
H N
12 6
2966, 1557 cm ; H NMR (400 MHz, DMSO-d
6 3
): δ 2.24 (s, CH ), 7.12
(
m, Ar-3H), 7.20 (d, J = 8.0 Hz, Ar-2H), 7.83 (d, J = 3.4 Hz, Ar-H), 9.90 (s,
1
3
7
-(4-Nitrobenzyl)pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine (8h)
Ar-H) ppm; C NMR (100 MHz, DMSO-d
127.38, 128.78, 129.11, 133.09, 134.23, 136.98, 140.94, 146.21; MS
(EI): m/z calcd. for [C13 S+H]: 315.06. Found: 315.
6
): δ 20.57, 100.80, 102.02,
Yellow solid, yield: 86%, m.p. 188–190°C. IR (film) υ: 3108, 3055,
−
1 1
1
637, 1513, 1251, 1074 cm ; H NMR (400 MHz, DMSO-d
s, N─CH ), 7.12 (m, Ar-3H), 7.71 (d, J = 8.0 Hz, Ar-2H), 7.83 (d,
J = 3.4 Hz, Ar-H), 9.90 (s, Ar-H); C NMR (100 MHz, DMSO-d
6
): δ 5.57
10 6 2
H N O
(
2
1
3
6
): δ
8.34, 100.80, 102.02, 121.38, 128.78, 129.11, 133.09, 134.23,
40.94, 146.21, 162.1; MS (EI): m/z calcd. for [C13 +H]: 296.1.
ACKNOWLEDGMENTS
4
1
H
10
N
7
O
2
Authors are thankful to the Department of Science and Technology,
New Delhi, India for financial support under Fast Track Young Scientist
Schemes and are grateful to the Principal and Head Department of
Chemistry for providing research facilities. Amit Choudhari (File No:
PDF/2016/003615) is grateful to the Science and Engineering
Research Board (SERB), Government of India, New Delhi for the
award of a National Post-Doctoral Fellowship.
Found: 296.
7
-(2′-Nitrile-1,1′-biphenylbenzyl)pyrrolo[3,2-e]tetrazolo[1,5-c]-
pyrimidine (8i)
−1
White solid, yield: 86%, m.p. 179–181°C. IR (film) υ: 3108, 3055 cm
;
1
6 2
H NMR (400 MHz, DMSO-d ): δ 5.73 (s, N─CH ), 7.16 (d, J = 3.4 Hz,