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Volumn , Issue 15, 2008, Pages 2257-2262

K-10 clay-catalyzed enol-driven decarboxylative ring-transformation approach to dihydro- and tetrahydroquinolines from carbohydrates

(4) Yadav, Lal Dhar Singh a Awasthi, Chhama a Rai, Vijai Kumar a Rai, Ankita a

a UNIVERSITY OF ALLAHABAD (India)

Author keywords

1,3 oxazin 2 ones(thiones); Carbohydrates; Microwaves; Mineral catalyzed; Quinolines; Solvent free

Indexed keywords

GLUCOSE; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; MICHAEL ADDITION; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SYNTHESIS;

EID: 53149098200 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078277 Document Type: Article

Times cited : (7)

References (62)

1
- 20144367831
- (a) Van Straten, N. C. R.; Van Berkel, T. H. J.; Demont, D. R.; Karstens, W.-J. F.; Merkx, R.; Oosterom, J.; Schulz, J.; Van Someren, R. G.; Timmers, C. M.; van Zandvoort, P. M. J. Med. Chem. 2005, 48, 1697.
- (2005) J. Med. Chem , vol.48 , pp. 1697
- Van Straten, N.C.R.¹ Van Berkel, T.H.J.² Demont, D.R.³ Karstens, W.-J.F.⁴ Merkx, R.⁵ Oosterom, J.⁶ Schulz, J.⁷ Van Someren, R.G.⁸ Timmers, C.M.⁹ van Zandvoort, P.M.¹⁰

2
- 14644404913
- (b) Gaillard, S.; Papamicael, C.; Marsais, F.; Dupas, G.; Levacher, V. Synlett 2005, 441.
- (2005) Synlett , pp. 441
- Gaillard, S.¹ Papamicael, C.² Marsais, F.³ Dupas, G.⁴ Levacher, V.⁵

3
- 0038606161
- (c) Foucaud, B.; Laube, B.; Schemm, R.; Kreimeyer, A.; Goeldner, M.; Betz, H. J. Biol. Chem. 2003, 278, 24011.
- (2003) J. Biol. Chem , vol.278 , pp. 24011
- Foucaud, B.¹ Laube, B.² Schemm, R.³ Kreimeyer, A.⁴ Goeldner, M.⁵ Betz, H.⁶

4
- 0142216387
- (d) Michael, J. P. Nat. Prod. Rep. 2003, 20, 476.
- (2003) Nat. Prod. Rep , vol.20 , pp. 476
- Michael, J.P.¹

5
- 0030602266
- (e) Katritzky, A.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
- (1996) Tetrahedron , vol.52 , pp. 15031
- Katritzky, A.¹ Rachwal, S.² Rachwal, B.³

6
- 0003455624
- 2nd ed, Pergamon: Oxford
- Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: Oxford, 2000, 616.
- (2000) Handbook of Heterocyclic Chemistry , pp. 616
- Katritzky, A.R.¹ Pozharskii, A.F.²

7
- 0004039074
- Georg Thieme Verlag: Stuttgart
- Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles: Georg Thieme Verlag: Stuttgart, 1995, 329.
- (1995) The Chemistry of Heterocycles , pp. 329
- Eicher, T.¹ Hauptmann, S.²

8
- 53149144173
- Patent ZA19710000791, 19710209, 1971
- Huber-Emden, H.; Hubele, A.; Klahre, G. Ger. Patent ZA19710000791, 19710209, 1971.
- Huber-Emden, H.¹ Hubele, A.² Klahre³ Ger, G.⁴

9
- 28844448733
- Samosorn, S.; Bremner, J. B.; Ball, A.; Lewis, K. Bioorg. Med. Chem. 2006, 14, 857.
- (2006) Bioorg. Med. Chem , vol.14 , pp. 857
- Samosorn, S.¹ Bremner, J.B.² Ball, A.³ Lewis, K.⁴

10
- 0032544311
- Maignan, S.; Guilloteau, J.; Zhou-Liu, Q.; Clément-Mella, C.; Mikol, V. J. Mol. Biol. 1998, 282, 359.
- (1998) J. Mol. Biol , vol.282 , pp. 359
- Maignan, S.¹ Guilloteau, J.² Zhou-Liu, Q.³ Clément-Mella, C.⁴ Mikol, V.⁵

11
- 0035045365
- (a) d'Angelo, J.; Mouscadet, F.; Desmäele, D.; Zouhiri, F.; Leh, H. Pathol. Biol. 2001, 49, 237.
- (2001) Pathol. Biol , vol.49 , pp. 237
- d'Angelo, J.¹ Mouscadet, F.² Desmäele, D.³ Zouhiri, F.⁴ Leh, H.⁵

12
- 0035851335
- (b) Zouhiri, F.; Desmäele, D.; d'Angelo, J.; Ourevitch, M.; Mouscadet, J. F.; Leh, H.; Bret, M. L. Tetrahedron Lett. 2001, 42, 8189.
- (2001) Tetrahedron Lett , vol.42 , pp. 8189
- Zouhiri, F.¹ Desmäele, D.² d'Angelo, J.³ Ourevitch, M.⁴ Mouscadet, J.F.⁵ Leh, H.⁶ Bret, M.L.⁷

13
- 53149098830
- U.S. Patent 20050025995A1, 2005
- (a) Cheng, C. H.; Chen, R. M.; Huang, C. W.; Yang, C. C. U.S. Patent 20050025995A1, 2005.
- Cheng, C.H.¹ Chen, R.M.² Huang, C.W.³ Yang, C.C.⁴

14
- 53149101537
- U.S. Patent 20050164031A1, 2005
- (b) Thompson, M. E.; Ma, B.; Djurovich, P. U.S. Patent 20050164031A1, 2005.
- Thompson, M.E.¹ Ma, B.² Djurovich, P.³

15
- 53149116523
- U.S. Patent 20050164030A1, 2005
- (c) Knowles, D. B.; Kwong, R. U.S. Patent 20050164030A1, 2005.
- Knowles, D.B.¹ Kwong, R.²

16
- 13644252174
- (d) Kim, J. L.; Shin, I. S.; Kim, H. J. Am. Chem. Soc. 2005, 127, 1614.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 1614
- Kim, J.L.¹ Shin, I.S.² Kim, H.³

17
- 0000226894
- (a) Agrawal, A. K.; Jenekhe, S. A. Chem. Mater. 1996, 8, 579.
- (1996) Chem. Mater , vol.8 , pp. 579
- Agrawal, A.K.¹ Jenekhe, S.A.²

18
- 0035833878
- (b) Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315.
- (2001) Macromolecules , vol.34 , pp. 7315
- Jenekhe, S.A.¹ Lu, L.² Alam, M.M.³

19
- 0033582781
- (a) Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499.
- (1999) Tetrahedron Lett , vol.40 , pp. 1499
- Cho, C.S.¹ Oh, B.H.² Shim, S.C.³

20
- 33748641983
- (b) Zhou, L.; Zhang, Y. J. Chem. Soc., Perkin Trans. 1 1998, 2899.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2899
- Zhou, L.¹ Zhang, Y.²

21
- 0026083923
- (c) Larock, R. C.; Kero, M.-Y. Tetrahedron Lett. 1991, 32, 569.
- (1991) Tetrahedron Lett , vol.32 , pp. 569
- Larock, R.C.¹ Kero, M.-Y.²

22
- 0012763354
- (d) Zhou, L.; Tu, S.; Shi, D.; Dai, G.; Chen, W. Synthesis 1988, 851.
- (1988) Synthesis , pp. 851
- Zhou, L.¹ Tu, S.² Shi, D.³ Dai, G.⁴ Chen, W.⁵

23
- 0000591888
- (e) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
- (1987) Tetrahedron Lett , vol.28 , pp. 5291
- Larock, R.C.¹ Babu, S.²

24
- 0000467055
- (f) Ozawa, F.; Yanagihara, H.; Yamamoto, A. J. Org. Chem. 1986, 51, 415.
- (1986) J. Org. Chem , vol.51 , pp. 415
- Ozawa, F.¹ Yanagihara, H.² Yamamoto, A.³

25
- 84944053662
- Katritzky, A. R, Rees, C. W, Eds, Pergamon: New York
- (g) Jones, G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: New York, 1996, 167.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 167
- Jones, G.¹

26
- 0002877215
- (h) Cho, C. S.; Oh, B. H.; Kim, T. J.; Kim, T. J.; Shim, S. C. Chem. Commun. 2000, 1885.
- (2000) Chem. Commun , pp. 1885
- Cho, C.S.¹ Oh, B.H.² Kim, T.J.³ Kim, T.J.⁴ Shim, S.C.⁵

27
- 0037184893
- (i) Jiang, B.; Si, Y. G. J. Org. Chem. 2002, 67, 9449.
- (2002) J. Org. Chem , vol.67 , pp. 9449
- Jiang, B.¹ Si, Y.G.²

28
- 0000476009
- (j) Skraup, H. Chem. Ber. 1880, 13, 2086.
- (1880) Chem. Ber , vol.13 , pp. 2086
- Skraup, H.¹

29
- 0001048571
- (k) Friedländer, P. Chem. Ber. 1882, 15, 2572.
- (1882) Chem. Ber , vol.15 , pp. 2572
- Friedländer, P.¹

30
- 0002261052
- (l) Mansake, R. H.; Kulka, M. Org. React. (N. Y.) 1953, 7, 59.
- (1953) Org. React. (N. Y.) , vol.7 , pp. 59
- Mansake, R.H.¹ Kulka, M.²

31
- 0025313308
- (m) Linderman, R. J.; Kirollos, K. S. Tetrahedron Lett. 1990, 31, 2689.
- (1990) Tetrahedron Lett , vol.31 , pp. 2689
- Linderman, R.J.¹ Kirollos, K.S.²

32
- 0037140878
- (n) Theoclitou, M. E.; Robinson, L. A. Tetrahedron Lett. 2002, 43, 3907.
- (2002) Tetrahedron Lett , vol.43 , pp. 3907
- Theoclitou, M.E.¹ Robinson, L.A.²

33
- 33947093958
- (a) Cortese, N. A.; Ziegler, C. B.; Hrnjez, B. J.; Heck, R. F. J. Org. Chem. 1978, 43, 2952.
- (1978) J. Org. Chem , vol.43 , pp. 2952
- Cortese, N.A.¹ Ziegler, C.B.² Hrnjez, B.J.³ Heck, R.F.⁴

34
- 33947093389
- (b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 5800
- Hegedus, L.S.¹ Allen, G.F.² Bozell, J.J.³ Waterman, E.L.⁴

35
- 0027464633
- (c) Kundu, N. G.; Mahanty, J. S.; Das, P.; Das, B. Tetrahedron Lett. 1993, 34, 1625.
- (1993) Tetrahedron Lett , vol.34 , pp. 1625
- Kundu, N.G.¹ Mahanty, J.S.² Das, P.³ Das, B.⁴

36
- 0032921440
- (d) Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1999, 401.
- (1999) Synlett , pp. 401
- Cacchi, S.¹ Fabrizi, G.² Marinelli, F.³

37
- 0000620613
- (a) Diamond, S. E.; Szalkiewicz, A.; Mares, F. J. Am. Chem. Soc. 1979, 101, 490.
- (1979) J. Am. Chem. Soc , vol.101 , pp. 490
- Diamond, S.E.¹ Szalkiewicz, A.² Mares, F.³

38
- 0003110384
- (b) Watanabe, Y.; Yamamoto, M.; Shim, S. C.; Mitsudo, T.; Takegami, Y. Chem. Lett. 1979, 8, 1025.
- (1979) Chem. Lett , vol.8 , pp. 1025
- Watanabe, Y.¹ Yamamoto, M.² Shim, S.C.³ Mitsudo, T.⁴ Takegami, Y.⁵

39
- 0001595977
- (c) Watanabe, Y.; Suzuki, N.; Shim, S. C.; Yamamoto, M.; Mitsudo, T.; Takegami, Y. Chem. Lett. 1980, 9, 429.
- (1980) Chem. Lett , vol.9 , pp. 429
- Watanabe, Y.¹ Suzuki, N.² Shim, S.C.³ Yamamoto, M.⁴ Mitsudo, T.⁵ Takegami, Y.⁶

40
- 0001471980
- (d) Boyle, W. J.; Mares, F. Organometallics 1982, 1, 1003.
- (1982) Organometallics , vol.1 , pp. 1003
- Boyle, W.J.¹ Mares, F.²

41
- 33845645895
- (e) Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E.; Verdecchia, M. Synlett 2006, 3218.
- (2006) Synlett , pp. 3218
- Abbiati, G.¹ Arcadi, A.² Marinelli, F.³ Rossi, E.⁴ Verdecchia, M.⁵

42
- 0002455286
- (a) Watanabe, Y.; Tsuji, Y.; Suzuki, N. Chem. Lett. 1981, 10, 1067.
- (1981) Chem. Lett , vol.10 , pp. 1067
- Watanabe, Y.¹ Tsuji, Y.² Suzuki, N.³

43
- 0001194811
- (b) Watanabe, Y.; Tsuji, Y.; Ohsugi, Y. Tetrahedron Lett. 1981, 22, 2667.
- (1981) Tetrahedron Lett , vol.22 , pp. 2667
- Watanabe, Y.¹ Tsuji, Y.² Ohsugi, Y.³

44
- 0020795498
- (c) Watanabe, Y.; Tsuji, Y.; Ohsugi, Y.; Shida, J. Bull. Chem. Soc. Jpn. 1983, 56, 2452.
- (1983) Bull. Chem. Soc. Jpn , vol.56 , pp. 2452
- Watanabe, Y.¹ Tsuji, Y.² Ohsugi, Y.³ Shida, J.⁴

45
- 0021372193
- (d) Watanabe, Y.; Tsuji, Y.; Shida, J. Bull. Chem. Soc. Jpn. 1984, 57, 435.
- (1984) Bull. Chem. Soc. Jpn , vol.57 , pp. 435
- Watanabe, Y.¹ Tsuji, Y.² Shida, J.³

46
- 0002892348
- (e) Tsuji, Y.; Nishimura, H.; Huh, K.-T.; Watanabe, Y. J. Organomet. Chem. 1985, 286, C44.
- (1985) J. Organomet. Chem , vol.286
- Tsuji, Y.¹ Nishimura, H.² Huh, K.-T.³ Watanabe, Y.⁴

47
- 33845281473
- (f) Tsuji, Y.; Huh, K.-T.; Watanabe, Y. J. Org. Chem. 1987, 59, 1673.
- (1987) J. Org. Chem , vol.59 , pp. 1673
- Tsuji, Y.¹ Huh, K.-T.² Watanabe, Y.³

48
- 34548240554
- (g) Mierde, H. V.; Ledoux, N.; Allaert, B.; Voort, P. V. D.; Drozdzak, R.; Vos, D. D.; Verpoort, F. New J. Chem. 2007, 31, 1572.
- (2007) New J. Chem , vol.31 , pp. 1572
- Mierde, H.V.¹ Ledoux, N.² Allaert, B.³ Voort, P.V.D.⁴ Drozdzak, R.⁵ Vos, D.D.⁶ Verpoort, F.⁷

49
- 34250636363
- (h) Martinez, R.; Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2007, 1599.
- (2007) Eur. J. Org. Chem , pp. 1599
- Martinez, R.¹ Ramón, D.J.² Yus, M.³

50
- 0001431068
- Watanabe, Y.; Takatsuki, K.; Shim, S. C.; Mitsudo, T.; Takegami, Y. Bull. Chem. Soc. Jpn. 1978, 51, 3397.
- (1978) Bull. Chem. Soc. Jpn , vol.51 , pp. 3397
- Watanabe, Y.¹ Takatsuki, K.² Shim, S.C.³ Mitsudo, T.⁴ Takegami, Y.⁵

51
- 37549035078
- (a) Yadav, L. D. S.; Rai, A.; Rai, V. K.; Awasthi, C. Tetrahedron Lett. 2008, 49, 687.
- (2008) Tetrahedron Lett , vol.49 , pp. 687
- Yadav, L.D.S.¹ Rai, A.² Rai, V.K.³ Awasthi, C.⁴

52
- 40649094805
- (b) Yadav, L. D. S.; Awasthi, C.; Rai, V. K.; Rai, A. Tetrahedron Lett. 2007, 48, 8033.
- (2007) Tetrahedron Lett , vol.48 , pp. 8033
- Yadav, L.D.S.¹ Awasthi, C.² Rai, V.K.³ Rai, A.⁴

53
- 34249808835
- (c) Yadav, L. D. S.; Rai, V. K. Tetrahedron 2007, 63, 6924.
- (2007) Tetrahedron , vol.63 , pp. 6924
- Yadav, L.D.S.¹ Rai, V.K.²

54
- 28844478353
- (d) Yadav, L. D. S.; Rai, V. K. Tetrahedron Lett. 2006, 47, 395.
- (2006) Tetrahedron Lett , vol.47 , pp. 395
- Yadav, L.D.S.¹ Rai, V.K.²

55
- 33646571195
- (e) Yadav, L. D. S.; Yadav, S.; Rai, V. K. Green Chem. 2006, 8, 455.
- (2006) Green Chem , vol.8 , pp. 455
- Yadav, L.D.S.¹ Yadav, S.² Rai, V.K.³

56
- 24944542811
- (f) Yadav, L. D. S.; Yadav, S.; Rai, V. K. Tetrahedron 2005, 61, 10013.
- (2005) Tetrahedron , vol.61 , pp. 10013
- Yadav, L.D.S.¹ Yadav, S.² Rai, V.K.³

57
- 34547632759
- (a) Yadav, L. D. S.; Rai, A.; Rai, V. K.; Awasthi, C. Synlett 2007, 1905.
- (2007) Synlett , pp. 1905
- Yadav, L.D.S.¹ Rai, A.² Rai, V.K.³ Awasthi, C.⁴

58
- 34250195358
- (b) Yadav, L. D. S.; Awasthi, C.; Rai, V. K.; Rai, A. Tetrahedron Lett. 2007, 48, 4899.
- (2007) Tetrahedron Lett , vol.48 , pp. 4899
- Yadav, L.D.S.¹ Awasthi, C.² Rai, V.K.³ Rai, A.⁴

59
- 18944381067
- Stevens, C. V, Verhé, R. G, Eds, John Wiley and Sons: Chichester, UK
- Renewable Bioresources: Scope and Modification for Non-Food Applications; Stevens, C. V.; Verhé, R. G., Eds.; John Wiley and Sons: Chichester, UK, 2004.
- (2004) Renewable Bioresources: Scope and Modification for Non-Food Applications

60
- 53149094216
- General Procedure for the Synthesis of 1,3-Oxazin-2-ones(thiones) 4: Thoroughly mixed D-xylose/D-glucose 1 (1 mmol, semicarbazide hydrochloride/thiosemicarbazide 2 (1 mmol, sodium acetate (1 mmol) and montmorillonite K-10 clay (0.10 g) in a 20-mL vial were subjected to microwave irradiation in a CEM Discover Focused Microwave Synthesis System for 10 min at 90°C. After completion of the reaction as indicated by TLC, H2O (10 mL) was added to precipitate the crude product, which was recrystallized from EtOH to afford analytically pure sample of 4. Characterization Data of Representative Compounds: Compound 4a: white solid; yield: 82, mp 145-148°C.
- 4S: C, 41.37; H, 4.46; N, 6.89. Found: C, 41.68; H, 4.31; N, 7.08.

61
- 0004247127
- John Wiley and Sons, Inc, New York
- Audrieth, L. F.; Ogg, B. A. The Chemistry of Hydrazines; John Wiley and Sons, Inc.: New York, 1951.
- (1951) The Chemistry of Hydrazines
- Audrieth, L.F.¹ Ogg, B.A.²

62
- 53149137287
- 6)

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