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1-(5-Methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethanone
(1f).18
5-Amino-1-(3-chloro-4-uorophenyl)-1H-1,2,3-triazole-4-car-
White solid; mp 118–120 ꢀC (ethanol); 7.55–7.53 (m, 3H, Ar-H), bonitrile (1s). White solid; mp 260–262 ꢀC (ethanol); IR (KBr,
7.51–7.43 (m, 2H, Ar-H), 2.72 (s, 3H, COCH3), 2.56 (s, 3H, CH3). cmꢁ1): nmax ¼ 3492, 3387, 3354, 3212, 2211, 1683, 1587, 1507; 1H
1-(1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)ethanone NMR (400 MHz, DMSO) dH: 8.37–8.35 (m, 1H, Ar-H), 8.35–8.33
1
(1g).19 White solid; mp 80–83 C (ethanol); H NMR (400 MHz, (m, 1H, Ar-H), 8.10–8.07 (m, 1H, Ar-H), 7.65–7.60 (m, 1H, Ar-H),
ꢀ
CDCl3)dH: 7.57–7.40 (m, 4H, Ar-H), 2.73 (s, 3H, COCH3), 2.40 (s, 3H, 6.97 (bs, 2H, NH2); 13C NMR (100 MHz, DMSO) d 151.21, 147.30,
CH3).
122.96, 122.69, 121.79, 121.71, 117.82, 117.60, 115.93; LCMS
1-(1-(3-Chloro-4-uorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl) (ESI): m/z ¼ 237.3848 [M+].
1
ethanone (1h).19 White solid; mp 95–96 C (ethanol); H NMR
(1-(4-Nitrophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl)(phenyl)
ꢀ
(400 MHz, CDCl3) dH: 7.44–7.24 (m, 3H, Ar-H), 2.62 (s, 3H, methanone (1t).20 White solid; mp 172–175 ꢀC (ethanol); 1H
COCH3), 2.47 (s, 3H, CH3).
NMR (400 MHz, CDCl3) dH: 8.21 (d, 2H, J ¼ 9.6 Hz, Ar-H), 7.86–
1-(1-Butyl-5-methyl-1H-1,2,3-triazol-4-yl)ethanone
(1i).18 7.63 (m, 5H, Ar-H), 7.51–7. 29 (m, 5H, Ar-H), 7.12 (d, 2H, J ¼ 8.8
Brown liquid; 1H NMR (400 MHz, CDCl3)dH:4.33–4.30 (t, 2H, J¼ 6.6 Hz, Ar-H).
Hz, CH2), 2.55 (s, 3H, COCH3), 2.19 (s, 3H, CH3), 1.88–1.84 (m, 2H,
CH2), 1.36–1.32 (m, 2H, CH2), 0.96–0.91 (t, 2H, J ¼ 6.2 Hz, CH2).
Single crystal X-ray structure determination of 5-Amino-1-(4-
bromophenyl)-1H-1,2,3-triazole-4-carbonitrile. See ESI.†
1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)ethanone
(1j).18
Brown liquid; 1H NMR (400 MHz, CDCl3) dH: 7.32–7.26 (m, 5H,
Ar-H), 5.44 (s, 2H, CH2), 2.61 (s, 3H, COCH3), 2.38 (s, 3H, CH3).
Ethyl 1-(4-bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carbox-
ylate (1k).19 White solid; mp 164–166 ꢀC (ethanol); 1H NMR (400
MHz, DMSO) dH: 7.85 (d, 2H, J ¼ 8.8 Hz, Ar-H), 7.60 (d, J ¼ 8.76
Hz, 2H, Ar-H), 4.31–4.36 (q, J ¼ 7.32 Hz, 2H, OCH2), 2.50 (s, 3H,
CH3), 1.29–1.33 (t, J ¼ 7.36 Hz, 3H, CH2 CH3).
Acknowledgements
HS and JS thank UGC, New Delhi, India for the grant of Junior
Research Fellowships.
References
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Ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbox-
ylate (1l).19 White solid; mp 90–92 ꢀC (ethanol); 7.56–7.36 (m, 4H,
Ar-H), 4.43–4.37 (q, J ¼ 7.32 Hz, 2H, OCH2), 2.39 (s, 3H, CH3),
1.40–1.36 (t, J ¼ 7.32 Hz, 3H, CH2 CH3).
Ethyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbox-
ylate (1m).19 White solid; mp 123–124 ꢀC (ethanol); 1H NMR
(400 MHz, CDCl3) dH: 8.44 (d, 2H, J ¼ 8.76 Hz, Ar-H), 7.71 (d, J ¼
8.8 Hz, 2H, Ar-H), 4.45–4.42 (q, J ¼ 7.32 Hz, 2H, OCH2), 2.66
(s, 3H, CH3), 1.44–1.40 (t, J ¼ 7.32 Hz, 3H, CH2 CH3).
Ethyl 1-(3-chloro-4-uorophenyl)-5-methyl-1H-1,2,3-triazole-
4-carboxylate (1n).19 White solid; mp 55–57 ꢀC (ethanol); 1H NMR
(400 MHz, CDCl3) dH: 7.55 (d, 1H, J ¼ 6.6 Hz, Ar-H), 7.33 (d, 2H, J ¼
6.6 Hz Ar-H), 4.41–4.46 (q, J ¼ 7.32 Hz, 2H, OCH2), 2.57 (s, 3H,
CH3), 1.40–1.43 (t, J ¼ 7.32 Hz, 3H, CH2 CH3).
Methyl
5-methyl-1-(4-bromophenyl)-1H-1,2,3-triazole-4-
carboxylate (1o).20 White solid; mp 204–206 ꢀC (ethanol); 1H
NMR (400 MHz, CDCl3) dH: 7.56 (d, 2H, J ¼ 6.68 Hz, Ar-H), 7.35
(d, 2H, J ¼ 6.4 Hz Ar-H), 4.50 (s, 3H, OCH3), 2.58 (s, 3H, CH3).
Methyl 5-methyl-1-(4-nitophenyl)-1H-1,2,3-triazole-4-carbox-
ylate (1p).20 White solid; mp 155–157 ꢀC (ethanol); 1H NMR
(400 MHz, CDCl3) dH: 7.68 (d, 2H, J ¼ 8.04 Hz, Ar-H), 7.31 (d, 2H,
J ¼ 7.76 Hz Ar-H), 4.53 (s, 3H, OCH3), 2.54 (s, 3H, CH3).
5-Amino-1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile
(1q). White solid; mp 240–242 ꢀC (ethanol); IR (KBr, cmꢁ1): nmax
¼ 3338, 3327, 3249, 3204, 2247, 1653, 1506; 1H NMR (400 MHz,
DMSO) dH: 7.77 (d, 2H, J ¼ 8.8 Hz, Ar-H), 7.49 (d, 2H, J ¼ 8.8 Hz,
Ar-H), 7.17 (bs, 2H, NH2); 13C NMR (100 MHz, DMSO) d 147.98,
133.23, 132.80, 127.18, 122.70, 113.34, 101.39; LCMS (ESI): m/z
¼ 264. 3532 [M+ + 2].
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5-Amino-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbonitrile
(1r).20 White solid; mp 205–207 ꢀC (ethanol); 1H NMR (400 MHz,
DMSO) dH: 8.41 (d, 2H, J ¼ 8.8 Hz, Ar-H), 7.92 (d, 2H, J ¼ 8.8 Hz,
Ar-H), 7.21 (bs, 2H, NH2).
RSC Adv.
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