PAPER
Efficient Conversion of Carboxylic Acids into N-Acylbenzotriazoles
2797
1H NMR: = 8.27–8.25 (m, 2 H), 8.14–8.11 (m, 2 H), 7.82–7.76 (m,
1 H), 7.66–7.60 (m, 1 H), 7.06–7.03 (m, 2 H).
1-(1H-1,2,3-Benzotriazol-1-yl)-3-phenyl-2-propyn-1-one (2l)
Yield: 92%; mp 124–125 °C.
13C NMR: = 165.2, 162.9, 145.0, 134.4, 131.9, 130.2, 126.2,
121.1, 119.8, 115.3, 114.3.
1H NMR: = 8.32 (d, J = 8.2 Hz, 1 H), 8.17 (d, J = 8.2 Hz, 1 H),
7.80 (d, J = 7.0 Hz, 2 H), 7.07 (t, J = 7.3 Hz, 1 H), 7.55 (t, J = 7.9
Hz, 2 H), 7.46 (t, J = 7.0 Hz, 2 H).
13C NMR: = 150.5, 146.4, 133.8, 131.8, 131.1, 130.7, 128.9,
126.8, 120.5, 119.2, 114.4, 96.2, 81.4.
Anal. Calcd for C13H9N3O2: C, 65.27; H, 3.79; N, 17.56. Found: C,
65.28; H, 3.73; N, 17.59.
1H-1,2,3-Benzotriazol-1yl(2-thienyl)methanone (2f)
Anal. Calcd for C15H9N3O: C, 72.86; H, 3.67; N, 16.99. Found: C,
72.72; H, 3.67; N, 16.95.
Yield: 97%; mp 173–175 °C (Lit.8 mp 175–176 °C).
1H NMR: = 8.50 (dd, J = 4.1, 1.3 Hz, 1 H), 8.34–8.28 (m, 3 H),
7.85–7.80 (m, 1 H), 7.68–7.63 (m, 1 H), 7.42 (dd, J = 5.0, 1.3 Hz, 1
1-(1H-1,2,3-Benzotriazol-1-yl)-2-chloro-1-propanone (2m)
H).
Yield: 86%; mp 87–88 °C.
13C NMR: = 158.7, 145.1, 138.7, 132.5, 131.6, 130.9, 128.5,
128.4, 126.7, 120.1, 114.4.
1H NMR: = 8.28 (d, J = 8.2 Hz, 1 H), 8.15 (d, J = 8.2 Hz, 1 H),
7.71 (td, J = 7.1, 1.0 Hz, 1 H), 7.55 (td, J = 8.2, 1.1 Hz, 1 H), 5.96
(q, J = 6.9 Hz, 1 H), 1.96 (d, J = 6.9 Hz, 3 H).
1H-1,2,3-Benzotriazol-1-yl(1H-indol-2-yl)methanone (2g)
Yield: 97%; mp 213–215 °C.
1H NMR: = 12.37 (br s, 1 H), 8.40 (d, J = 8.2 Hz, 1 H), 8.33 (d,
J = 8.2 Hz, 1 H), 8.03 (d, J = 1.3 Hz, 1 H), 7.86–7.81 (m, 2 H), 7.68–
7.59 (m, 2 H), 7.93 (t, J = 7.6 Hz, 1 H), 7.16 (t, J = 7.5 Hz, 1 H).
13C NMR: = 168.1, 146.2, 131.1, 130.9, 126.7, 120.4, 114.3, 51.1,
20.8.
Anal. Calcd for C9H8ClN3O: C, 51.56; H, 3.85; N, 20.04. Found: C,
51.76; H, 3.72; N, 20.18.
13C NMR: = 158.7, 145.2, 138.7, 132.1, 131.2, 127.3, 127.1,
127.0, 126.9, 123.5, 121.2, 120.4, 114.9, 114.7, 113.2.
1-(1H-1,2,3-Benzotriazol-1-yl)-2-bromo-1-ethanone (2n)
Yield: 87%; mp 91–92 °C.
Anal. Calcd for C15H10N4O: C, 68.68; H, 3.85; N, 21.36. Found: C,
68.44; H, 3.67; N, 21.29.
1H NMR: = 8.26 (d, J = 8.2 Hz, 1 H), 8.15 (d, J = 8.2 Hz, 1 H),
7.73–7.68 (m, 1 H), 7.58–7.52 (m, 1 H), 4.92 (s, 2 H).
13C NMR: = 165.0, 146.3, 130.9, 126.7, 120.4, 114.2, 26.5.
1-(1H-1,2,3-Benzotriazol-1-yl)-2-methyl-2-propen-1-one (2h)
Yield: 83%; colorless oil.
Anal. Calcd for C8H6BrN3O: C, 40.03; H, 2.52; N, 17.50. Found: C,
40.52; H, 2.30; N, 17.43.
1H NMR: = 8.27 (d, J = 8.2 Hz, 1 H), 8.13 (d, J = 8.2 Hz, 1 H),
7.69–7.64 (m, 1 H), 7.52 (td, J = 8.1, 1.0 Hz, 1 H), 6.28 (s, 1 H),
6.08–6.07 (m, 1 H), 2.29 (d, J = 0.9 Hz, 3 H).
13C NMR: = 167.5, 145.7, 137.2, 132.0, 130.2, 129.6, 126.1,
120.0, 114.5, 19.8.
1-(1H-1,2,3-Benzotriazol-1-yl)-2,2-dichloro-1-ethanone (2o)
Yield: 86%; mp 87–88 °C.
1H NMR: = 8.29 (d, J = 8.2 Hz, 1 H), 8.18 (d, J = 8.2 Hz, 1 H),
7.76 (t, J = 7.1 Hz, 1 H), 7.61 (t, J = 8.1 Hz, 1 H), 7.54 (s, 1 H).
Anal. Calcd for C10H9N3O: C, 64.16; H, 4.85; N, 22.45. Found: C,
63.82; H, 4.71; N, 22.35.
13C NMR: = 161.5, 146.4, 131.4, 130.9, 127.2, 120.8, 114.2, 63.5.
Anal. Calcd for C8H5Cl2N3O: C, 41.77; H, 2.19; N, 18.27. Found:
C, 42.01; H, 2.17; N, 18.16.
(E)-1-(1H-1,2,3-Benzotriazol-1-yl)-2-buten-1-one (2i)
Yield: 86%; mp 87–88 °C.
1H NMR: = 8.31 (d, J = 8.2 Hz, 1 H), 8.10 (d, J = 8.2 Hz, 1 H),
7.65–7.60 (m, 1 H), 7.50–7.43 (m, 3 H), 2.12 (d, J = 5.2 Hz, 3 H).
13C NMR: = 163.3, 149.7, 146.1, 131.2, 130.0, 125.9, 121.3,
119.9, 114.5, 18.7.
1-(1H-1,2,3-Benzotriazol-1-yl)-2-methoxy-1-ethanone (2p)
Yield: 96%; mp 103–104 °C.
1H NMR: = 8.28 (d, J = 8.2 Hz, 1 H), 8.12 (d, J = 8.2 Hz, 1 H),
7.71–7.65 (m, 1 H), 7.56–7.50 (m, 1 H), 5.15 (s, 2 H), 3.66 (s, 3 H).
13C NMR: = 168.6, 145.7, 130.8, 130.6, 126.3, 120.1, 114.0, 71.1,
59.8.
Anal. Calcd for C10H9N3O: C, 64.16; H, 4.85; N, 22.45. Found: C,
64.29; H, 4.97; N, 22.52.
Anal. Calcd for C9H9N3O2: C, 56.54; H, 4.74; N, 21.98. Found: C,
56.55; H, 4.76; N, 21.92.
(E)-1-(1H-1,2,3-Benzotriazol-1-yl)-3-phenyl-2-propen-1-one
(2j)
Yield: 96%; mp 151–152 °C (Lit.7 mp 158–159 °C).
1-(1H-1,2,3-Benzotriazol-1-yl)-2-(phenylsulfanyl)-1-ethanone
(2q)
Yield: 90%; mp 63–64 °C.
1H NMR: = 8.24–8.21 (m, 1 H), 8.12–8.09 (m, 1 H), 7.66–7.6 (m,
1 H), 7.53–7.47 (m, 3 H), 7.32–7.24 (m, 3 H), 4.66 (s, 2 H).
13C NMR: = 167.6, 146.1, 133.8, 131.0, 131.0, 130.5, 129.1,
127.6, 126.3, 120.2, 114.2, 37.9.
1H NMR: = 8.40 (d, J = 8.2 Hz, 1 H), 8.16–8.12 (m, 3 H), 7.76–
7.64 (m, 3 H), 7.55–7.45 (m, 4 H).
13C NMR: = 163.9, 148.7, 146.3, 134.1, 131.4, 130.2, 129.1,
129.0, 126.2, 120.1, 116.0, 114.8.
1-(1H-1,2,3-Benzotriazol-1-yl)-2-propyn-1-one (2k)
Yield: 83%; mp 99–100 °C.
1H NMR: = 8.24 (d, J = 8.2 Hz, 1 H), 8.16 (d, J = 8.4 Hz, 1 H),
7.74–7.68 (m, 1 H), 7.56 (td, J = 8.2, 1.0 Hz, 1 H), 3.72 (s, 1 H).
13C NMR: = 149.2, 146.2, 130.9,130.6, 126.9, 120.5, 114.1, 83.9,
74.5.
Anal. Calcd for C14H11N3OS: C, 62.43; H, 4.12; N, 15.60. Found:
C, 62.73; H, 4.05; N, 15.67.
1-(1H-1,2,3-Benzotriazol-1-yl)-2-phenyl-1,2-ethanedione (2r)
Yield: 72%; mp 72–73 °C.
1H NMR: = 8.36 (d, J = 8.1 Hz, 1 H), 8.18 (d, J = 8.2 Hz, 1 H),
8.03–8.00 (m, 2 H), 7.80–7.69 (m, 2 H), 6.63–7.53 (m, 3 H).
Anal. Calcd for C9H5N3O: C, 63.16; H, 2.94; N, 24.55. Found: C,
63.16; H, 2.87; N, 24.80.
Synthesis 2003, No. 18, 2795–2798 © Thieme Stuttgart · New York