JOURNAL OF CHEMICAL RESEARCH 2017 613
1
13
1
698 (3 × C=O); H NMR δ 2.39 (3H, s, CH ), 3.73 (1H, d, J = 8.8 Hz,
8.04–8.08 (1H, m, ArH); C NMR δ 30.3 (CH ), 38.3 (CH), 44.1 (CH),
3
3
CH), 4.08 (1H, d, J = 8.8 Hz, CH), 7.31–7.37 (5H, m, 5 × ArH),
.80–7.88 (3H, m, 3 × ArH), 8.00–8.02 (1H, m, ArH); C NMR δ 30.3
CH ), 42.5 (CH), 43.9 (CH), 47.1, 122.9, 123.0, 128.2, 128.3, 129.1,
46.3, 122.9, 123.3, 125.2, 128.9, 129.4, 131.8, 133.6, 135.4, 135.6, 141.5,
142.1, 148.9, 194.1, 194.5, 199.4; MS m/z (%): 369 (5); Anal. calcd for
C H ClNO : C, 61.72; H, 3.27; N, 3.79; found: C, 61.84; H, 3.38; N,
13
7
(
3
19 12
5
1
32.1, 135.2, 135.3, 141.9, 141.9, 193.7, 194.0, 199.7; MS m/z (%): 290
3.90%.
(7); Anal. calcd for C H O : C, 78.61; H, 4.86; found: C, 78.76; H,
19
14
3
2-Acetyl-3-(2-nitrophenyl)-spiro[cyclopropane-1,2’-indene]-
’,3’-dione (5f): Dark brown powder; m.p. 149–151 °C; IR (ν , cm–1)
4
.95%.
1
max
2
-Acetyl-3-(4-chlorophenyl)-spiro[cyclopropane-1,2’-indene]-
1
KBr: 1736, 1711, 1694, (3 × C=O). H NMR δ 2.36 (3H, s, CH ), 3.69
3
–
1
1
’,3’-dione (5b): Violet powder; m.p. 157–159 °C; IR (ν , cm ) KBr:
max
1
(1H, d, J = 8.8 Hz, CH), 4.02 (1H, d, J = 8.8 Hz, CH), 7.46–7.55 (2H,
1735, 1708, 1692 (3 × C=O); H NMR δ 2.37 (3H, s, CH ), 3.68 (1H, d,
3
m, 2 × ArH), 7.85–7.92 (4H, m, 4 × ArH), 8.02–8.04 (1H, m, ArH);
J = 8.8 Hz, CH), 4.02 (1H, d, J = 8.8 Hz, CH), 7.23 (2H, d, J = 8.0 Hz, 2
13
C NMR δ 30.4 (CH ), 39.2 (CH), 43.4 (CH), 46.2, 123.2, 123.3,
3
×
ArH), 7.30 (2H, d, J = 8.0 Hz, 2 × ArH), 7.81–7.89 (3H, m, 3 × ArH),
126.4, 126.9, 131.8, 132.8, 133.78, 135.8, 135.8, 141.7, 141.9, 147.5,
13
8
4
.00–8.02 (1H, m, ArH); C NMR δ 30.3 (CH ), 41.3 (CH), 43.8 (CH),
3
1
6
93.4, 193.8, 198.2; MS m/z (%): 335 (7); Anal. calcd for C H NO : C,
8.06; H, 3.91; N, 4.18; found: C, 68.17; H, 4.06; N, 4.30%.
19
13
3
6.8, 123.0, 123.1, 128.6, 130.4, 130.6, 134.1, 135.4, 135.4, 141.9, 193.6,
194.7, 199.2; MS m/z (%): 324 (5); Anal. calcd for C H ClO : C,
19 13 3
7
0.27; H, 4.03; found: C, 70.40; H, 4.14%.
-(2-Acetyl-1’,3’-dioxo-1’,3’-dihydrospiro-[cyclopropane-1,2’-
inden]-3-yl)benzonitrile (5c): Grey powder; m.p. 103–105 °C; IR (νmax,
Received 11 September 2017; accepted 26 September 2017
Paper 1704997
Published online: 5 October 2017
4
–1
1
cm ) KBr: 1733, 1711, 1685 (3 × C=O); H NMR δ 2.37 (3H, s, CH ),
3
3.70 (1H, d, J = 8.8 Hz, CH), 4.06 (1H, d, J = 8.8 Hz, CH), 7.42 (2H,
d, J = 8.4 Hz, 2 × ArH), 7.63 (2H, d, J = 8.4 Hz, 2 × ArH), 7.84–7.91
13
References
(
3H, m, 3 × ArH), 8.01–8.03 (1H, m, ArH); C NMR δ 30.4 (CH ),
3
4
0.6 (CH), 43.5 (CH), 46.5, 112.0, 118.5, 123.1, 123.2, 130.0, 132.1,
35.7, 137.6, 141.7, 141.8, 193.4, 194.2, 198.6; MS m/z (%): 315 (3);
Anal. calcd for C H NO : C, 76.18; H, 4.16; N, 4.44; found: C, 76.29;
1
2
3
T. Ye and M.A. McKervey, Chem. Rev., 1994, 94, 1091.
G. Bartoli, G. Bencivenni and R. Dalpozzo, Synthesis, 2014, 46, 979.
T. Ferrary, E. David, G. Milanole, T. Besset, P. Jubault and X. Pannecuucke,
Org. Lett., 2013, 15, 5598.
1
2
0
13
3
H, 4.27; N, 4.53%.
-Acetyl-3-(4-bromophenyl)-spiro[cyclopropane-1,2’-indene]-
4
V.K. Aggarwal, H.W. Smith, R.V.H. Jones and R. Fieldhouse, Chem.
Commun., 1997, 18, 1785.
2
–1
1
’,3’-dione (5d): Brown powder; m.p. 161–163 °C; IR (ν , cm )
max
1
5
6
7
8
A. Hartikka and P.I. Arvidsson, J. Org. Chem., 2007, 72, 5874.
A. Nefzi, J.M. Ostresh and R.A. Houghten, Chem. Rev., 1997, 97, 449.
L.A. Thompson, Curr. Opin. Chem. Biol., 2000, 4, 324.
E. Gontier, N. Boussouel, C. Terrasse, M. Jannoyer, M. Menard, B.
Thomasset and F. Bourgaud, Biochem. Soc. Trans., 2000, 28, 578.
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Chem. Lett., 1996, 6, 1029.
KBr: 1736, 1709, 1690 (3 × C=O); H NMR δ 2.37 (3H, s, CH ), 3.67
3
(
1H, d, J = 8.8 Hz, CH), 4.00 (1H, d, J = 8.8 Hz, CH), 7.17 (2H, d,
J = 8.0 Hz, 2 × ArH), 7.46 (2H, d, J = 8.0 Hz, 2 × ArH), 7.81–7.89 (3H,
13
m, 3 × ArH), 8.00–8.02 (1H, m, ArH); C NMR δ 30.3 (CH ), 41.4
3
9
(
1
CH), 43.7 (CH), 46.8, 122.3, 123.0, 123.1, 130.8,131.1, 131.5, 135.4,
35.5, 141.8, 193.6, 194.6, 199.2; MS m/z (%): 369 (8); Anal. calcd for
C H BrO : C, 61.81; H, 3.55; found: C, 61.96; H, 3.70%.
10
G. Bose, K. Bracht, P.J. Bednarski, M. Lalk and P. Langer, Bioorg. Med.
Chem., 2006, 14, 4694.
19
13
3
2
-Acetyl-3-(4-chloro-3-nitrophenyl)-spiro[cyclopropane-1,2’-
1
12
1
J. Salaun and M.S. Bair, Curr. Med. Chem., 1995, 2, 511.
K.-M. Qiu, H.-H. Wang, L.-M. Wang, Y. Luo, X.-H. Yang, X.-M. Wang and
H.-L. Zhu, Bioorg. Med. Chem., 2012, 20, 2010.
indene]-1’,3’-dione (5e): Brown powder; m.p. 199–201 °C; IR (νmax,
–
1
1
cm ) KBr: 1737, 1713, 1695 (3 × C=O); H NMR δ 2.40 (3H, s, CH ),
3
3
.62 (1H, d, J = 8.8 Hz, CH), 4.22 (1H, d, J = 8.8 Hz, CH), 7.52–7.59
13 J. Banothu, S. Basavoju, and R. Bavantula, J. Heterocycl. Chem., 2015,
52, 853.
(
2H, m, 2 × ArH), 7.80–7.90 (3H, m, 3 × ArH), 8.06 (1H, s, ArH),