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Volumn , Issue 20, 2007, Pages 3107-3112

An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives

(4) Das, Biswanath a Laxminarayana, Keetha a Krishnaiah, Maddeboina a Srinivas, Yallamalla a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

2 naphthol; Aldehydes; Cyclic 1,3 dicarbonyl compounds; NaHSO4 SiO2; Three component condensation reaction; Xanthene

Indexed keywords

2 NAPHTHOL; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 37749004900 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990922 Document Type: Article

Times cited : (125)

References (46)

1
- 37749039367
- Part 130 in the series 'Studies on novel synthetic methodologies'.
- Part 130 in the series 'Studies on novel synthetic methodologies'.

2
- 1542272290
- (a) Chetia, A.; Saikia, C. J.; Lekhok, K. C.; Boruah, R. C. Tetrahedron Lett. 2004, 45, 2649.
- (2004) Tetrahedron Lett , vol.45 , pp. 2649
- Chetia, A.¹ Saikia, C.J.² Lekhok, K.C.³ Boruah, R.C.⁴

3
- 7044237277
- (b) Devi, I.; Bhuyan, P. J. Tetrahedron Lett. 2004, 45, 8625.
- (2004) Tetrahedron Lett , vol.45 , pp. 8625
- Devi, I.¹ Bhuyan, P.J.²

4
- 0038726005
- (c) Wang, L. M.; Xia, J.; Qin, F.; Qian, C.; Sun, J. Synthesis 2003, 1241.
- (2003) Synthesis , pp. 1241
- Wang, L.M.¹ Xia, J.² Qin, F.³ Qian, C.⁴ Sun, J.⁵

5
- 33750309194
- (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
- (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 259
- Trost, B.M.¹

6
- 1242341296
- (a) Prajapati, D.; Sandhu, J. S. Synlett 2004, 235.
- (2004) Synlett , pp. 235
- Prajapati, D.¹ Sandhu, J.S.²

7
- 5144226547
- (b) Bose, A. K.; Pednekar, S.; Ganguly, S. N.; Chakraborty, G.; Manhas, M. S. Tetrahedron Lett. 2004, 45, 8351.
- (2004) Tetrahedron Lett , vol.45 , pp. 8351
- Bose, A.K.¹ Pednekar, S.² Ganguly, S.N.³ Chakraborty, G.⁴ Manhas, M.S.⁵

8
- 0001363457
- (a) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 7842
- Keating, T.A.¹ Armstrong, R.W.²

9
- 0031852604
- (b) Yamada, T.; Omote, Y.; Yamanaka, Y.; Miyazawa, T.; Kuwata, S. Synthesis 1998, 991.
- (1998) Synthesis , pp. 991
- Yamada, T.¹ Omote, Y.² Yamanaka, Y.³ Miyazawa, T.⁴ Kuwata, S.⁵

10
- 0037157803
- (c) Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127.
- (2002) Tetrahedron , vol.58 , pp. 6127
- Ross, G.F.¹ Herdtweck, E.² Ugi, I.³

11
- 13844250294
- (a) Akiyama, T.; Matsuda, K.; Fuchibe, K. Synlett 2005, 322.
- (2005) Synlett , pp. 322
- Akiyama, T.¹ Matsuda, K.² Fuchibe, K.³

12
- 0142091320
- Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. III Synlett 2003, 1906.
- (b) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. III Synlett 2003, 1906.

13
- 0033615750
- (c) Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
- (1999) Tetrahedron Lett , vol.40 , pp. 7831
- Akiyama, T.¹ Takaya, J.² Kagoshima, H.³

14
- 85080850876
- (d) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1045.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 1045
- Arend, M.¹ Westermann, B.² Risch, N.³

15
- 0036642529
- Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
- (2002) Tetrahedron , vol.58 , pp. 5367
- Van de Water, R.W.¹ Pettus, T.R.R.²

16
- 33751554625
- (a) Wolff, A.; Boechmer, V.; Vogt, W.; Ugozzoli, F.; Andreetti, G. D. J. Org. Chem. 1990, 55, 5665.
- (1990) J. Org. Chem , vol.55 , pp. 5665
- Wolff, A.¹ Boechmer, V.² Vogt, W.³ Ugozzoli, F.⁴ Andreetti, G.D.⁵

17
- 0028842782
- (b) No, K. W.; Kim, J. E.; Kwon, K. M. Tetrahedron Lett. 1995, 36, 8453.
- (1995) Tetrahedron Lett , vol.36 , pp. 8453
- No, K.W.¹ Kim, J.E.² Kwon, K.M.³

18
- 8844222050
- (c) Mashraqui, S. H.; Patil, M. B.; Mistry, H. D.; Ghadigaonkar, S.; Meetsma, A. Chem. Lett. 2004, 33, 1058.
- (2004) Chem. Lett , vol.33 , pp. 1058
- Mashraqui, S.H.¹ Patil, M.B.² Mistry, H.D.³ Ghadigaonkar, S.⁴ Meetsma, A.⁵

19
- 0000293463
- (a) Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651.
- (1975) Chem. Rev , vol.75 , pp. 651
- Desimoni, G.¹ Tacconi, G.²

20
- 0030122802
- (b) Wan, P.; Backer, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C. Can. J. Chem. 1996, 74, 465.
- (1996) Can. J. Chem , vol.74 , pp. 465
- Wan, P.¹ Backer, B.² Diao, L.³ Fischer, M.⁴ Shi, Y.⁵ Yang, C.⁶

21
- 0038273169
- (c) Turner, A. B. Q. Rev., Chem. Soc. 1964, 18, 347.
- (1964) Q. Rev., Chem. Soc , vol.18 , pp. 347
- Turner, A.B.¹

22
- 0006092785
- (d) Schleigh, W. R. Org. Chem. Bull. 1971, 43, 1.
- (1971) Org. Chem. Bull , vol.43 , pp. 1
- Schleigh, W.R.¹

23
- 30744455580
- (a) Gardner, P. D. J. Am. Chem. Soc. 1959, 51, 3364.
- (1959) J. Am. Chem. Soc , vol.51 , pp. 3364
- Gardner, P.D.¹

24
- 0030833252
- (b) Angle, S. R.; Rainer, J. D.; Woytowiez, C. J. Org. Chem. 1997, 62, 5884.
- (1997) J. Org. Chem , vol.62 , pp. 5884
- Angle, S.R.¹ Rainer, J.D.² Woytowiez, C.³

25
- 0001642827
- (c) Merijan, A.; Gardner, P. D. J. Org. Chem. 1965, 30, 3965.
- (1965) J. Org. Chem , vol.30 , pp. 3965
- Merijan, A.¹ Gardner, P.D.²

26
- 0017796644
- Poupelin, J. P.; Saint-Ruf, G.; Foussard-Blanpin, O.; Marcisse, G.; Uchida-Ernouf, G.; Lacroix, R. Eur. J. Med. Chem. 1978, 13, 67.
- (1978) Eur. J. Med. Chem , vol.13 , pp. 67
- Poupelin, J.P.¹ Saint-Ruf, G.² Foussard-Blanpin, O.³ Marcisse, G.⁴ Uchida-Ernouf, G.⁵ Lacroix, R.⁶

27
- 37749015142
- Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. PCT Int. Appl. WO9706178, 1997.
- Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. PCT Int. Appl. WO9706178, 1997.

28
- 37749007866
- Hideo, T, Teruomi, J, Sankyo Co, Jpn. Patent 56005480, 1981
- Hideo, T.; Teruomi, J. (Sankyo Co.) Jpn. Patent 56005480, 1981.

29
- 17144375787
- (a) Saint-Ruf, G.; De, A..; Hieu, H. T. Bull. Chim. Ther. 1972, 7, 83.
- (1972) Bull. Chim. Ther , vol.7 , pp. 83
- Saint-Ruf, G.¹ De, A.² Hieu, H.T.³

30
- 0016697518
- (b) Saint-Ruf, G.; Hieu, H. T.; Poupelin, J. P. Naturwissenschaften 1975, 62, 584.
- (1975) Naturwissenschaften , vol.62 , pp. 584
- Saint-Ruf, G.¹ Hieu, H.T.² Poupelin, J.P.³

31
- 17144387077
- (a) Ion, R. M. Prog. Catal. 1997, 2, 55.
- (1997) Prog. Catal , vol.2 , pp. 55
- Ion, R.M.¹

32
- 0032253115
- (b) Ion, R. M.; Frackowiak, D.; Planner, A.; Wiktorowicz, K. Acta Biochim. Pol. 1998, 45, 833.
- (1998) Acta Biochim. Pol , vol.45 , pp. 833
- Ion, R.M.¹ Frackowiak, D.² Planner, A.³ Wiktorowicz, K.⁴

33
- 84859109802
- (a) Banerjee, A.; Mukherjee, A. K. Stain Technol. 1981, 56, 83.
- (1981) Stain Technol , vol.56 , pp. 83
- Banerjee, A.¹ Mukherjee, A.K.²

34
- 37749025902
- US Patent 6583168
- (b) Menchen, S. M.; Benson, S. C.; Lam, J. Y. L.; Zhen, W.; Sun, D.; Rosenblum, B. B.; Khan, S. H.; Taing, M. US Patent 6583168, 2003.
- (2003)
- Menchen, S.M.¹ Benson, S.C.² Lam, J.Y.L.³ Zhen, W.⁴ Sun, D.⁵ Rosenblum, B.B.⁶ Khan, S.H.⁷ Taing, M.⁸

35
- 0024559378
- Knight, C. G.; Stephens, T. Biochem. J. 1989, 258, 683.
- (1989) Biochem. J , vol.258 , pp. 683
- Knight, C.G.¹ Stephens, T.²

36
- 17144431996
- (a) Siirkecioglu, O.; Talinli, N.; Akar, A. J. Chem. Res., Synop. 1995, 502.
- (1995) J. Chem. Res., Synop , pp. 502
- Siirkecioglu, O.¹ Talinli, N.² Akar, A.³

37
- 0037036547
- (b) Ahmad, M.; King, T. A.; Ko, D.-K.; Cha, B. H.; Lee, J. J. Phys. D: Appl. Phys. 2002, 35, 1473.
- (2002) J. Phys. D: Appl. Phys , vol.35 , pp. 1473
- Ahmad, M.¹ King, T.A.² Ko, D.-K.³ Cha, B.H.⁴ Lee, J.⁵

38
- 33746025668
- (a) Das, B.; Ravikanth, B.; Ramu, R.; Laxminarayana, K.; Rao, B. V. J. Mol. Catal. A.: Chem. 2006, 255, 74.
- (2006) J. Mol. Catal. A.: Chem , vol.255 , pp. 74
- Das, B.¹ Ravikanth, B.² Ramu, R.³ Laxminarayana, K.⁴ Rao, B.V.⁵

39
- 33845889080
- (b) Das, B.; Laxminarayana, K.; Ravikanth, B.; Rao, B. R. J. Mol. Catal. A: Chem. 2007, 261, 180.
- (2007) J. Mol. Catal. A: Chem , vol.261 , pp. 180
- Das, B.¹ Laxminarayana, K.² Ravikanth, B.³ Rao, B.R.⁴

40
- 0041336709
- (a) Ramesh, C.; Ravindranath, N.; Das, B. J. Org. Chem. 2003, 68, 7101.
- (2003) J. Org. Chem , vol.68 , pp. 7101
- Ramesh, C.¹ Ravindranath, N.² Das, B.³

41
- 0037429053
- (b) Ramesh, C.; Mahender, G.; Ravindranath, N.; Das, B. Tetrahedron Lett. 2003, 44, 1465.
- (2003) Tetrahedron Lett , vol.44 , pp. 1465
- Ramesh, C.¹ Mahender, G.² Ravindranath, N.³ Das, B.⁴

42
- 4444290141
- (c) Das, B.; Banerjee, J.; Ravindranath, N. Tetrahedron 2004, 60, 8357.
- (2004) Tetrahedron , vol.60 , pp. 8357
- Das, B.¹ Banerjee, J.² Ravindranath, N.³

43
- 33745698149
- (d) Das, B.; Ravinder Reddy, K.; Thirupathi, P. Tetrahedron Lett. 2006, 47, 5855.
- (2006) Tetrahedron Lett , vol.47 , pp. 5855
- Das, B.¹ Ravinder Reddy, K.² Thirupathi, P.³

44
- 33748757231
- (e) Das, B.; Venkateswarlu, K.; Krishnaiah, M.; Holla, H. Tetrahedron Lett. 2006, 47, 7551.
- (2006) Tetrahedron Lett , vol.47 , pp. 7551
- Das, B.¹ Venkateswarlu, K.² Krishnaiah, M.³ Holla, H.⁴

45
- 0001516761
- Breton, G. W. J. Org. Chem. 1997, 62, 8952.
- (1997) J. Org. Chem , vol.62 , pp. 8952
- Breton, G.W.¹

46
- 37749022216
- General Procedure for the Synthesis of 12-Aryl- or 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives: NaHSO4·SiO2 (100 mg) was added to a mixture of 2-naphthol (1.0 mmol, aldehyde (1.0 mmol) and dimedone (1.2 mmol) in DCE (5 mL, The mixture was stirred at reflux conditions and the reaction was monitored by TLC. After completion of the reaction, the mixture was filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, 3% EtOAc in hexane) to afford the pure 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivative. Spectral data of some representative products are given below: Compound 3b: 1H NMR (200 MHz, CDCl3, δ, 7.86 (dd, J, 2.0, 8.0 Hz, 1 H, 7.75 (dd, J, 2.0, 8.0 Hz, 2 H, 7.11-7.46 (m, 7 H, 5.62 (s, 1 H, 2.63 (s, 2 H, 2.31 (d, J, 12.0 Hz, 1 H, 2.20 d, J, 12.0 Hz, 1 H
- +..

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