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The Journal of Organic Chemistry
1ꢀ(12ꢀBenzoylꢀ5,7ꢀdihydroindolo[2,3ꢀb]carbazolꢀ6ꢀyl)propanꢀ
ACKNOWLEDGMENT
1
2
3
4
5
6
7
8
1ꢀone (9g). The compound was prepared following GPꢀIII emꢀ
ploying phenyl glyoxal (1 mmol), indole (2.1 mmol) and heptaneꢀ
3,5ꢀdione (1 mmol). Purification by column chromatography
(10% pet etherꢀEtOAc) afforded the title compound as deep yelꢀ
low solid (295mg, 0.71 mmol, 71% yield). M.P. 280ꢀ282 °C (deꢀ
composed). 1H NMR (300 MHz, DMSOꢀd6): δ 1.09ꢀ1.14 (m,
3H), 3.01ꢀ3.05 (m, 2H), 6.88ꢀ6.93 (m, 2H), 7.16ꢀ7.21 (m, 2H),
7.31ꢀ7.41 (m, 6H), 7.56 (t, J= 7.5 Hz, 1H), 7.99 (d, J= 7.5 Hz,
2H), 10.09 (s, 2H); 13C NMR (75 MHz, DMSOꢀd6): δ 7.5, 36.9,
103.3, 111.0, 114.9, 120.4, 120.7, 120.9, 125.2, 129.2, 130.0,
132.6, 134.7, 135.8, 139.3, 139.8, 198.93, 198.99; FTꢀIR (KBr,
cmꢀ1): 733.8, 1152.3, 1239.9, 1320.5, 1464.4, 1593.9, 1644.7,
2923.9, 3335.4, 3389.4; HRMS (ESIꢀTOF) m/z Calcd for
C28H21N2O2 [M+H]: 417.1603, found 417.1576.
Research funding by D. S. Kothari, UGC (TD), CSIR (SRF to SD
and RM) and SERB (SR/S1/OCꢀ05/2012), India are gratefully
acknowledged.
REFERENCES
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12ꢀBenzoylꢀ5,7ꢀdihydroindolo[2,3ꢀb]carbazoleꢀ6ꢀcarbonitrile
(9h). The compound was prepared following GPꢀIII employing
phenyl glyoxal (1 mmol), indole (2.1 mmol) and malononitrile (1
mmol). Purification by column chromatography (15% pet etherꢀ
EtOAc) afforded the title compound as deep yellow solid (262
(3) (a) Liu, J.; He, T.; Wang, L. Tetrahedron 2011, 67, 3420ꢀ3426. (b)
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1
mg, 0.68 mmol, 68% yield). M.P. 296ꢀ290 °C; H NMR (300
MHz, DMSOꢀd6): δ 5.76ꢀ5.81 (m, 2H), 6.09ꢀ6.14 (m, 4H), 6.26ꢀ
6.35 (m, 4H), 6.47 (t, J= 7.5 Hz, 2H), 6.72 (d, J= 7.5 Hz, 1H),
11.14 (s, 2H); 13C NMR (75 MHz, DMSOꢀd6): δ 74.2, 111.2,
112.9, 115.2, 119.5, 119.6, 120.4, 125.2, 129.0, 129.1, 131.3,
134.6, 134.8, 140.1, 140.4, 196.7; FTꢀIR (KBr, cmꢀ1): 731.3,
1248.0, 1327.7, 1462.3, 1608.6, 1644.5, 2221.5, 2923.5, 3287.3,
3435.7; HRMS (ESIꢀTOF) m/z Calcd for C26H16N3O [M+H]:
386.1293, found 386.1322.
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4952. (d) Levesque, I.; Bertrand, P. O.; Blouin, N.; Leclerc, M.; Zecchin,
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12ꢀBenzoylꢀNꢀphenylꢀ5,7ꢀdihydroindolo[2,3ꢀb]carbazoleꢀ6ꢀ
carboxamide (9i). The compound was prepared following GPꢀIII
employing phenyl glyoxal (1 mmol), indole (2.1 mmol) and N,Nꢀ
diphenylmalonamide (1 mmol). Purification by column chromaꢀ
tography (8% pet etherꢀEtOAc) afforded the title compound as
deep yellow solid (311 mg, 0.65 mmol, 65% yield). M.P. 80ꢀ82
1
°C; H NMR (300 MHz, DMSOꢀd6): δ 7.01 (t, J= 7.5 Hz, 2H),
7.22 (t, J= 7.2 Hz, 1H), 7.33ꢀ7.52 (m, 6H), 7.58 (t, J= 7.5 Hz,
2H), 7.66 (d, J= 8.1 Hz, 2H), 7.74 (d, J= 7.2 Hz, 1H), 8.01 (d, J=
4.5 Hz, 4H), 10.79 (s, 1H), 11.58 (s, 2H); 13C NMR (75 MHz,
DMSOꢀd6): δ 101.2, 111.1, 113.4, 118.5, 119.5, 120.1, 120.3,
123.1, 124.6, 127.8, 128.0, 128.3, 128.9, 129.0, 134.2, 135.4,
136.8, 139.1, 140.4, 164.1, 197.6; FTꢀIR (KBr, cmꢀ1): 689.9,
739.1, 1245.2, 1322.3, 1439.4, 1462.3, 1501.1, 1596.0, 1644.0,
2851.6, 2922.0, 3361.8; HRMS (ESIꢀTOF) m/z calcd for
C32H22N3O2 [M+H]: 480.1712, found 480.1715.
ASSOCIATED CONTENT
Supporting Information
This material is available free of charge via the Internet at
Materials and methods, optimization Table, general procedures,
characterization data for all compounds, 1H and 13C spectra of the
new compounds, single crystal XRD data, and MidꢀIRꢀATR data
and spectra.
AUTHOR INFORMATION
Corresponding Author
(11) (a) Li, Z.; Duan, Z.; Kang, J.; Wang, H.; Yu, L.; Wu, Y. Tetraheꢀ
dron, 2008, 64, 1924ꢀ1930. (b) Prakash, G. K. S.; Panja, C.; Shakhmin,
A.; Shah, E.; Mathew, T.; Olah, G. A. J. Org. Chem. 2009, 74, 8659–
8668. (c) Jaratjaroonphong, J.; Sathalalai, S.; Techasauvapak, P.;
Reutrakul, V. Tetrahedron Lett. 2009, 50, 6012–6015. (d) Zhang, J.; Belꢀ
lomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc.
2012, 134, 13765−13772. (e) Zhang, J.; Bellomo, A.; Trongsiriwat, N.;
Jia, T.; Carroll, P. J.; Dreher, S. D.; Tudge, M. T.; Yin, H.; Robinson, J.
R.; Schelter, E. J.; Walsh, P. J. J. Am. Chem. Soc. 2014, 136, 6276−6287.
Professor Dilip K. Maiti, eꢀmail: catalysisandmateriꢀ
Notes
The authors declare no competing financial interests.
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