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Volumn , Issue 13, 2007, Pages 2086-2090

Regioselective synthesis of functionally crowded benzenes at room temperature through ring transformation of 2H-pyran-2-ones

(3) Singh, Fateh Veer a Kumar, Vijay a Goel, Atul a

a CENTRAL DRUG RESEARCH INSTITUTE (India)

Author keywords

2H pyran 2 one; Benzene; Malononitrile; Ring transformation reaction

Indexed keywords

2H PYRAN 2 ONE; BENZENE DERIVATIVE; LACTONE; MALONONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; ROOM TEMPERATURE; SYNTHESIS;

EID: 34548191557 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984885 Document Type: Article

Times cited : (13)

References (59)

1
- 34548185146
- C.D.R.I. Communication No 7224.
- C.D.R.I. Communication No 7224.

2
- 34548187207
- Modern Arene Chemistiy; Astrue, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
- (a) Modern Arene Chemistiy; Astrue, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002.

3
- 13444292181
- (b) Xi, C.; Chen, C.; Lin, J.; Hong, X. Org. Lett. 2005, 7, 347.
- (2005) Org. Lett , vol.7 , pp. 347
- Xi, C.¹ Chen, C.² Lin, J.³ Hong, X.⁴

4
- 0001667095
- (c) Katritzky, A. R.; Belyakov, S. A.; Henderson, S. A.; Steel, P. J. J. Org. Chem. 1997, 62, 8215.
- (1997) J. Org. Chem , vol.62 , pp. 8215
- Katritzky, A.R.¹ Belyakov, S.A.² Henderson, S.A.³ Steel, P.J.⁴

5
- 1542607786
- (d) Covarrubias-Zuniga, A.; Rios-Barrios, E. J. Org. Chem. 1997, 62, 5688.
- (1997) J. Org. Chem , vol.62 , pp. 5688
- Covarrubias-Zuniga, A.¹ Rios-Barrios, E.²

6
- 0001113283
- (a) Olah, G. A. Acc. Chem. Res. 1971, 4, 240.
- (1971) Acc. Chem. Res , vol.4 , pp. 240
- Olah, G.A.¹

7
- 33947449188
- (b) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
- (1951) Chem. Rev , vol.49 , pp. 273
- Bunnett, J.F.¹ Zahler, R.E.²

8
- 34548186169
- (a) Negishi, E. Acc. Chem. Res. 1982, 11, 413.
- (1982) Acc. Chem. Res , vol.11 , pp. 413
- Negishi, E.¹

9
- 3743119954
- (b) Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031.
- (1988) Chem. Rev , vol.88 , pp. 1031
- Brown, J.M.¹ Cooley, N.A.²

10
- 0026699017
- (c) Mitchell, T. N. Synthesis 1992, 803.
- (1992) Synthesis , pp. 803
- Mitchell, T.N.¹

11
- 4243055272
- (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2497.
- (1995) Chem. Rev , vol.95 , pp. 2497
- Miyaura, N.¹ Suzuki, A.²

12
- 20544450502
- 1st ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
- (e) Metal-Catalyzed Cross-Coupling Reactions, Vol. 1, 1st ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
- (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1

13
- 20544450502
- 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
- (f) Metal-Catalyzed Cross-Coupling Reactions, Vol. 2, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
- (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.2

14
- 33845555248
- (a) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
- (1982) Acc. Chem. Res , vol.15 , pp. 306
- Beak, P.¹ Snieckus, V.²

15
- 0001248031
- (b) Chauder, B.; Green, L.; Snieckus, V. Pure Appl. Chem. 1999, 71, 1521.
- (1999) Pure Appl. Chem , vol.71 , pp. 1521
- Chauder, B.¹ Green, L.² Snieckus, V.³

16
- 34248227306
- and references cited therein
- (c) Chen, G.; Lam, W. H.; Fok, W. S.; Lee, H. W.; Kwong, F. Y. Chem. Asian J. 2007, 2, 306; and references cited therein.
- (2007) Chem. Asian J , vol.2 , pp. 306
- Chen, G.¹ Lam, W.H.² Fok, W.S.³ Lee, H.W.⁴ Kwong, F.Y.⁵

17
- 33846918696
- (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
- (2007) Chem. Rev , vol.107 , pp. 174
- Alberico, D.¹ Scott, M.E.² Lautens, M.³

18
- 34548182027
- (b) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 3541.
- (2007) Aldrichimica Acta , vol.40 , pp. 3541
- Campeau, L.-C.¹ Stuart, D.R.² Fagnou, K.³

19
- 34247537463
- (c) Goossen, L. G.; Rodriguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 4824
- Goossen, L.G.¹ Rodriguez, N.² Melzer, B.³ Linder, C.⁴ Deng, G.⁵ Levy, L.M.⁶

20
- 34248384892
- (d) Becht, J.-M.; Catala, C.; Drian, C. L.; Wagner, A. Org. Lett. 2007, 9, 1781.
- (2007) Org. Lett , vol.9 , pp. 1781
- Becht, J.-M.¹ Catala, C.² Drian, C.L.³ Wagner, A.⁴

21
- 0012397313
- (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
- (1990) Chem. Rev , vol.90 , pp. 879
- Snieckus, V.¹

22
- 0000079033
- (b) Maggi, R.; Schlosser, M. J. Org. Chem. 1996, 61, 5430.
- (1996) J. Org. Chem , vol.61 , pp. 5430
- Maggi, R.¹ Schlosser, M.²

23
- 23044477413
- Chotana, G. A.; Rak, M. A.; Smith, M. R. J. Am. Chem. Soc. 2005, 127, 10539.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 10539
- Chotana, G.A.¹ Rak, M.A.² Smith, M.R.³

24
- 3042654141
- Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 1871
- Walker, S.D.¹ Barder, T.E.² Martinelli, J.R.³ Buchwald, S.L.⁴

25
- 9344240844
- Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. J. Am. Chem. Soc. 2004, 126, 15195.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 15195
- Altenhoff, G.¹ Goddard, R.² Lehmann, C.W.³ Glorius, F.J.⁴

26
- 0000676625
- Bamfield, P.; Gordon, P. F. Chem. Soc. Rev. 1984, 13, 441.
- (1984) Chem. Soc. Rev , vol.13 , pp. 441
- Bamfield, P.¹ Gordon, P.F.²

27
- 0038524273
- (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
- (1999) Chem. Soc. Rev , vol.28 , pp. 187
- Dötz, K.H.¹ Tomuschat, P.²

28
- 0041365922
- (b) Wang, H.; Huang, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 8980.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 8980
- Wang, H.¹ Huang, J.² Wulff, W.D.³ Rheingold, A.L.⁴

29
- 0037067028
- (c) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002, 124, 6512.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 6512
- Vorogushin, A.V.¹ Wulff, W.D.² Hansen, H.-J.³

30
- 0025102523
- (a) Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. J.; Miller, R. F. J. Am. Chem. Soc. 1990, 112, 3093.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 3093
- Danheiser, R.L.¹ Brisbois, R.G.² Kowalczyk, J.J.³ Miller, R.F.⁴

31
- 0001173186
- (b) Danheiser, R. L.; Gee, S. K. J. Org. Chem. 1984, 49, 1672.
- (1984) J. Org. Chem , vol.49 , pp. 1672
- Danheiser, R.L.¹ Gee, S.K.²

32
- 0042125423
- (a) Xi, Z.; Sato, K.; Gao, Y.; Lu, J.; Takahashi, T. J. Am. Chem. Soc. 2003, 125, 9568.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 9568
- Xi, Z.¹ Sato, K.² Gao, Y.³ Lu, J.⁴ Takahashi, T.⁵

33
- 0037160425
- (b) Takahashi, T.; Ishikawa, M.; Huo, S. J. Am. Chem. Soc. 2002, 124, 388.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 388
- Takahashi, T.¹ Ishikawa, M.² Huo, S.³

34
- 0034250675
- (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
- (2000) Chem. Rev , vol.100 , pp. 2901
- Saito, S.¹ Yamamoto, Y.²

35
- 14944380049
- (b) Bonaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gauthier, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 3473
- Bonaga, L.V.R.¹ Zhang, H.-C.² Moretto, A.F.³ Ye, H.⁴ Gauthier, D.A.⁵ Li, J.⁶ Leo, G.C.⁷ Maryanoff, B.E.⁸

36
- 0042734705
- (a) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 10921
- Asao, N.¹ Nogami, T.² Lee, S.³ Yamamoto, Y.⁴

37
- 0037202125
- (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 12650
- Asao, N.¹ Takahashi, K.² Lee, S.³ Kasahara, T.⁴ Yamamoto, Y.⁵

38
- 2942682670
- (c) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 7458
- Asao, N.¹ Aikawa, H.² Yamamoto, Y.³

39
- 33644678153
- Lee, M. J.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Tetrahedron 2006, 62, 3128.
- (2006) Tetrahedron , vol.62 , pp. 3128
- Lee, M.J.¹ Lee, K.Y.² Park, D.Y.³ Kim, J.N.⁴

40
- 0141539238
- (a) Langer, P.; Bose, G. Angew. Chem. Int. Ed. 2003, 42, 4033.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4033
- Langer, P.¹ Bose, G.²

41
- 0033538620
- (b) Katritzky, A. R.; Li, J.; Xie, L. Tetrahedron 1999, 55, 8263.
- (1999) Tetrahedron , vol.55 , pp. 8263
- Katritzky, A.R.¹ Li, J.² Xie, L.³

42
- 33746675087
- (c) Park, D. Y.; Kim, S. J.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2006, 47, 6315.
- (2006) Tetrahedron Lett , vol.47 , pp. 6315
- Park, D.Y.¹ Kim, S.J.² Kim, T.H.³ Kim, J.N.⁴

43
- 33846592371
- (d) Park, D. Y.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2007, 48, 1633.
- (2007) Tetrahedron Lett , vol.48 , pp. 1633
- Park, D.Y.¹ Lee, K.Y.² Kim, J.N.³

44
- 0027205468
- (a) Sadek, K. U.; Selim, M. A.; Elmaghraby, M. A.; Elnagdi, M. H. Pharmazie 1993, 48, 419.
- (1993) Pharmazie , vol.48 , pp. 419
- Sadek, K.U.¹ Selim, M.A.² Elmaghraby, M.A.³ Elnagdi, M.H.⁴

45
- 0026568258
- (b) Hartke, K.; Sauerbier, M.; Richter, W. F. Arch. Pharm. (Weinheim. Ger.) 1992, 325, 279.
- (1992) Arch. Pharm. (Weinheim. Ger.) , vol.325 , pp. 279
- Hartke, K.¹ Sauerbier, M.² Richter, W.F.³

46
- 0042505084
- (c) Gewald, K.; Schaefer, H. Z. Chem. 1981, 21, 183.
- (1981) Z. Chem , vol.21 , pp. 183
- Gewald, K.¹ Schaefer, H.²

47
- 0001503216
- Victory, P.; Borrell, J. I.; Vidal-Ferran, A.; Montenegro, E.; Jimeno, M. L. Heterocycles 1993, 36, 2273.
- (1993) Heterocycles , vol.36 , pp. 2273
- Victory, P.¹ Borrell, J.I.² Vidal-Ferran, A.³ Montenegro, E.⁴ Jimeno, M.L.⁵

48
- 0033574450
- Yu, Z.; Velasco, D. Tetrahedron Lett. 1999, 40, 3229.
- (1999) Tetrahedron Lett , vol.40 , pp. 3229
- Yu, Z.¹ Velasco, D.²

49
- 0003049435
- Harmata, M, Ed, JAI Press: Greenwich USA
- (a) Woodward, B. T.; Posner, G. H. Advances in Cycloaddition, Vol. 5; Harmata, M., Ed.; JAI Press: Greenwich USA, 1999, 47.
- (1999) Advances in Cycloaddition , vol.5 , pp. 47
- Woodward, B.T.¹ Posner, G.H.²

50
- 85027879301
- (b) Posner, G. H.; Afarinkia, K.; Dai, H. Org. Synth. 1995, 73, 231.
- (1995) Org. Synth , vol.73 , pp. 231
- Posner, G.H.¹ Afarinkia, K.² Dai, H.³

51
- 13844306924
- and references cited therein
- (c) Afarinkia, K.; Bearpark, M. J.; Ndibwami, A. J. Org. Chem. 2005, 70, 1122; and references cited therein.
- (2005) J. Org. Chem , vol.70 , pp. 1122
- Afarinkia, K.¹ Bearpark, M.J.² Ndibwami, A.³

52
- 15444378960
- Goel, A.; Singh, F. V.; Sharon, A.; Maulik, P. R. Synlett 2005, 623.
- (2005) Synlett , pp. 623
- Goel, A.¹ Singh, F.V.² Sharon, A.³ Maulik, P.R.⁴

53
- 23944462485
- Goel, A.; Singh, F. V.; Verma, D. Synlett 2005, 2027.
- (2005) Synlett , pp. 2027
- Goel, A.¹ Singh, F.V.² Verma, D.³

54
- 11144258848
- Goel, A.; Dixit, M.; Verma, D. Tetrahedron Lett. 2005, 46, 491.
- (2005) Tetrahedron Lett , vol.46 , pp. 491
- Goel, A.¹ Dixit, M.² Verma, D.³

55
- 30744475976
- (a) Goel, A.; Verma, D.; Dixit, M.; Raghunandan, R.; Maulik, P. R. J. Org. Chem. 2006, 71, 804.
- (2006) J. Org. Chem , vol.71 , pp. 804
- Goel, A.¹ Verma, D.² Dixit, M.³ Raghunandan, R.⁴ Maulik, P.R.⁵

56
- 34248172376
- (b) Goel, A.; Singh, F. V.; Dixit, M.; Verma, D.; Raghunandan, R.; Maulik, P. R. Chem. Asian J. 2007, 2, 239.
- (2007) Chem. Asian J , vol.2 , pp. 239
- Goel, A.¹ Singh, F.V.² Dixit, M.³ Verma, D.⁴ Raghunandan, R.⁵ Maulik, P.R.⁶

57
- 84986531968
- Tominaga, Y.; Ushirogochi, A.; Matsuda, Y. J. Heterocycl. Chem. 1987, 24, 1557.
- (1987) J. Heterocycl. Chem , vol.24 , pp. 1557
- Tominaga, Y.¹ Ushirogochi, A.² Matsuda, Y.³

58
- 34548151147
- General Procedure for the Synthesis of 5 and 7: A mixture of 5-alkyl-/5,6-dialkyl-3-cyano-4-methylsulfanyl-2H-pyran-2-ones 3 or 6-isopropyl-4-sec-amino-2H-pyran-2-ones 6 (1 mmol, malononitrile (1.2 mmol) and powdered KOH (1.2 mmol) in anhyd DMF (5 mL) was stirred at r.t. for 8-12 h. After completion of the reaction, the reaction mixture was poured into ice-water with vigorous stirring and finally neutralized with dilute HCl. The solid thus obtained was filtered and purified on a neutral alumina column using CHCl3-hexane (1:9) as eluent. 5a: yield: 89, white solid; mp 236-238°C. 1H NMR (200 MHz, CDCl 3, δ, 2.48 (s, 3 H, Me, 2.54 (s, 3 H, SMe, 5.10 (br s, 2 H, NH2, 6.42 (s, 1 H, ArH, 13C NMR (50.0 MHz, CDCl 3, DMSO, δ, 19.95, 26.68, 96.73, 98.40, 118.95, 119.83, 120.87, 152.67, 155.72, 158.00. IR (KBr, 2213 (CN, 3353, 3442 (NH2) cm
- 4O: 270.1481; found: 270.1483.

59
- 34548168552
- General Procedure for the Synthesis of 6: A mixture of compound 3d (1.0 mmol) and secondary amine (1.2 mmol) was refluxed in MeOH (20 mL) for 6-8 h. After completion of the reaction, MeOH was evaporated under vacuum, and the reaction mixture was washed with ice-cooled H2O. The crude was purified on a silica gel column using CHCl3 as eluent. 6a: yield 74, white solid; mp 162-164°C. 1H NMR (200 MHz, CDCl 3, δ, 1.23 (d, J, 6.8 Hz, 6 H, 2 x Me, 2.00-2.10 (m, 4 H, 2 x CH2, 2.62-2.73 (m, 1 H, CH, 3.54-3.62 (m, 2 H, CH 2, 4.02-4.10 (m, 2 H, CH2, 5.71 (s, 1 H, CH, 13C NMR (75.5 MHz, CDCl3, δ, 20.36, 34.00, 49.89, 66.99, 73.24, 94.52, 117.63, 161.92, 163.11, 172.59. IR (KBr, 1704 (CO, 2207 (CN) cm-1. MS ESI, m/z, 249 [M, 1
- + + 1].

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