G
S. Chuprun et al.
Paper
Synthesis
(2-Phenyl-2H-tetrazol-5-yl)(thiophen-2-yl)methanone (3p)
1H NMR (400 MHz, CDCl3): = 8.38–8.29 (m, 4 H), 7.80–7.71 (m, 2 H),
Prepared from 2-diazo-1-(thiophen-2-yl)ethan-1-one (5j)18 and ben-
7.56–7.45 (m, 2 H).
13C NMR (101 MHz, CDCl3): = 181.0, 162.4, 150.5 (q, J = 1.9 Hz),
134.5, 134.1, 132.2, 130.2, 122.2 (q, J = 1.2 Hz), 122.0, 120.3 (q, J =
259.0 Hz).
zenediazonium tosylate (4a).
Beige solid; yield: 54 mg (70%); mp 109.5–110.8 °C.
1H NMR (400 MHz, CDCl3): = 8.68 (dd, J = 3.9, 1.1 Hz, 1 H), 8.32–8.24
(m, 2 H), 7.89 (dd, J = 4.9, 1.2 Hz, 1 H), 7.68–7.56 (m, 3 H), 7.30 (dd, J =
5.0, 3.9 Hz, 1 H).
HRMS-ESI: m/z calcd for C15H8BrF3N4O2Na [M + Na]: 434.9675; found:
434.9692.
13C NMR (101 MHz, CDCl3): = 173.7, 162.1, 141.8, 137.1, 136.7,
136.4, 130.7, 129.9, 128.8, 120.4.
Naphthalen-1-yl(2-(4-(trifluoromethyl)phenyl)-2H-tetrazol-5-
yl)methanone (3u)
Prepared from 2-diazo-1-(naphthalen-1-yl)ethan-1-one (5o)18 and 4-
(trifluoromethyl)benzenediazonium tosylate (4g).
HRMS-ESI: m/z calcd for C12H8N4OSNa [M + Na]: 279.0311; found:
279.0319.
Beige solid; yield: 91 mg (82%); mp 144.8–146.6 °C (dec).
(1-Methyl-1H-pyrrol-2-yl)(2-phenyl-2H-tetrazol-5-yl)methanone
(3q)
1H NMR (400 MHz, CDCl3): = 8.75 (d, J = 8.5 Hz, 1 H), 8.41 (d, J = 8.5
Hz, 2 H), 8.28–8.12 (m, 2 H), 7.98 (dd, J = 8.1, 1.5 Hz, 1 H), 7.90 (d, J =
8.5 Hz, 2 H), 7.70 (ddd, J = 8.5, 6.8, 1.5 Hz, 1 H), 7.66–7.59 (m, 2 H).
Prepared from 2-diazo-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-one
(5k)21 and benzenediazonium tosylate (4a).
13C NMR (101 MHz, CDCl3): = 184.3, 163.9, 138.7, 134.7, 133.9,
132.7, 132.5 (q, J = 33.2 Hz), 132.4, 131.0, 128.8, 128.7, 127.2 (q, J = 3.7
Hz), 126.9, 125.4, 124.7, 124.2, 123.3 (q, J = 272.6 Hz), 120.6.
Beige solid; yield: 53 mg (70%); mp 82.0–83.3 °C (dec).
1H NMR (400 MHz, CDCl3): = 8.24 (dt, J = 6.4, 1.3 Hz, 2 H), 7.82 (dd,
J = 4.3, 1.7 Hz, 1 H), 7.66–7.51 (m, 3 H), 7.05 (t, J = 2.1 Hz, 1 H), 6.29
(dd, J = 4.3, 2.4 Hz, 1 H), 4.12 (s, 3 H).
HRMS-ESI: m/z calcd for C19H11F3N4ONa [M + Na]: 391.0777; found:
391.0795.
13C NMR (101 MHz, CDCl3): = 170.9, 163.5, 136.6, 133.8, 130.3,
129.8, 129.6, 124.9, 120.2, 109.5, 38.1.
Benzo[d][1,3]dioxol-5-yl(2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-
2H-tetrazol-5-yl)methanone (3v)
HRMS-ESI: m/z calcd for C13H11N5ONa [M + Na]: 276.0856; found:
276.0861.
Prepared from 1-(benzo[d][1,3]dioxol-5-yl)-2-diazoethan-1-one
(5p)18 and 2,3-dihydrobenzo[b][1,4]dioxine-6-diazonium tosylate
(4i).
Morpholino(2-(4-(trifluoromethoxy)phenyl)-2H-tetrazol-5-
yl)methanone (3r)
Prepared from 2-diazo-1-morpholinoethan-1-one (5l)22 and 4-(tri-
fluoromethoxy)benzenediazonium tosylate (4h).
Light orange solid; yield: 79 mg (75%); mp 151.2–151.9 °C (dec).
1H NMR (400 MHz, CDCl3): = 8.19 (dd, J = 8.3, 1.8 Hz, 1 H), 7.88 (d, J =
1.8 Hz, 1 H), 7.77 (d, J = 2.6 Hz, 1 H), 7.72 (dd, J = 8.8, 2.6 Hz, 1 H), 7.05
(d, J = 8.8 Hz, 1 H), 6.96 (d, J = 8.3 Hz, 1 H), 6.12 (s, 2 H), 4.36 (s, 4 H).
13C NMR (101 MHz, CDCl3): = 180.3, 162.4, 153.1, 148.3, 145.5,
144.2, 130.2, 130.1, 128.3, 118.2, 113.6, 110.0, 109.9, 108.2, 102.1,
64.5, 64.4.
Yellowish amorphous solid; yield: 44 mg (43%).
1H NMR (400 MHz, CDCl3): = 8.33–8.22 (m, 2 H), 7.46 (d, J = 8.7 Hz, 2
H), 3.96–3.89 (m, 4 H), 3.88–3.83 (m, 2 H), 3.83–3.76 (m, 2 H).
13C NMR (101 MHz, CDCl3): = 160.1, 157.2, 150.3 (q, J = 1.8 Hz),
134.5, 122.2, 121.8, 120.3 (q, J = 255.2 Hz), 66.9, 66.7, 47.6, 43.1.
HRMS-ESI: m/z calcd for C17H12N4O5Na [M + Na]: 375.0700; found:
375.0728.
HRMS-ESI: m/z calcd for C13H12F3N5O3Na [M + Na]: 366.0784; found:
366.0804.
(4-(5-(3-Nitrobenzoyl)-2H-tetrazol-2-yl)phenyl)(piperidin-1-
yl)methanone (3w)
Prepared from 2-diazo-1-(3-nitrophenyl)ethan-1-one (5q)18 and 4-
(piperidin-1-ylcarbonyl)benzenediazonium tosylate (4j).
2-(4-(Adamantan-1-yl)phenyl)-N,N-diethyl-2H-tetrazole-5-car-
boxamide (3s)
Prepared from 2-diazo-N,N-diethylacetamide (5m)23 and 4-
((3R,5R,7R)-adamantan-1-yl)benzenediazonium tosylate (4k).
Yellow solid; yield: 82 mg (67%); mp 132.1–134.3 °C (dec).
Pale yellow, amorphous solid; yield: 20 mg (18%).
1H NMR (400 MHz, CDCl3): = 9.36 (t, J = 2.0 Hz, 1 H), 8.81 (dt, J = 7.8,
1.4 Hz, 1 H), 8.57 (ddd, J = 8.3, 2.3, 1.1 Hz, 1 H), 8.39–8.27 (m, 2 H),
7.83 (t, J = 8.0 Hz, 1 H), 7.73–7.65 (m, 2 H), 3.76 (br s, 2 H), 3.40 (br s, 2
H), 1.91–1.49 (m, 6 H).
13C NMR (101 MHz, CDCl3): = 179.9, 168.3, 161.8, 148.5, 139.2,
136.6, 136.5, 136.1, 130.1, 128.7, 128.5, 125.7, 120.5, 48.8, 43.3, 26.6,
25.6, 24.5.
1H NMR (400 MHz, CDCl3): = 8.17–8.06 (m, 2 H), 7.63–7.51 (m, 2 H),
3.63 (dq, J = 21.1, 7.1 Hz, 4 H), 2.21–2.10 (m, 3 H), 2.03–1.92 (m, 6 H),
1.89–1.75 (m, 6 H), 1.32 (td, J = 7.1, 2.0 Hz, 6 H).
13C NMR (101 MHz, CDCl3): = 160.5, 158.6, 153.9, 134.1, 126.3,
119.8, 43.4, 43.0, 40.9, 36.6, 36.5, 28.8, 14.6, 12.7.
HRMS-ESI: m/z calcd for C22H29N5ONa [M + Na]: 402.2264; found:
402.2272.
HRMS-ESI: m/z calcd for C20H19N6O4 [M + H]: 407.1462; found:
407.1481.
(4-Bromophenyl)(2-(4-(trifluoromethoxy)phenyl)-2H-tetrazol-5-
yl)methanone (3t)
Prepared from 1-(4-bromophenyl)-2-diazoethan-1-one (5n)18 and
4-(trifluoromethoxy)benzenediazonium tosylate (4h).
Morpholino(2-phenyl-2H-tetrazol-5-yl)methanone (3x)
Prepared from 2-diazo-1-morpholinoethan-1-one (5l)22 and ben-
zenediazonium tosylate (4a).
Pale yellow solid; yield: 95 mg (77%); mp 113.6–116.3 °C.
Beige solid; yield: 32 mg (41%); mp 88.5–89.6 °C.
© 2019. Thieme. All rights reserved. — Synthesis 2019, 51, A–H