'On water' synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS)

Tetrahedron Letters

Volumn 49, Issue 27, 2008, Pages 4269-4271

  Sharma, Gaurav ^a   Kumar, Raj ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

1,3 Diaryl 2,3 dihydro 1,5 benzothiazepines; 1,3 Diarylpropenones; 2 Aminothiophenol; Catalysis; SDS; Water

Indexed keywords

1,3 DIARYL 2 PROPENONE DERIVATIVE; 2 AMINOTHIOPHENOL; 2,4 DIARYL 2,3 DIHYDRO 1,5 BENZOTHIAZEPINE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; DODECYL SULFATE SODIUM; KETONE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 44349151476     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.146     Document Type: Article

References (52)

1. Anticonvulsant:. Sarro G.D., Chimirri A., Sarro A.D., Gitto R., Grasso S., and Zappalá M. Eur. J. Med. Chem. 30 (1995) 925-929
2. +2 channel antagonist:. Kurokawa J., Adachi-Akahane S., and Nagao T. Eur. J. Pharmacol. 325 (1997) 229-232
3. Anti-HIV:. Grandolini G., Perioli L., and Ambrogi V. Eur. J. Med. Chem. 34 (1999) 701-709
4. Squalene synthetase inhibitor:. Yang X., Buzon L., Hamanaka E., and Liu K.K.-C. Tetrahedron: Asymmetry 11 (2000) 4447-4451 and the references cited therein
5. V2 Arginine vasopressin receptor antagonist:. Urbanski M.J., Chen R.H., Demarest K.T., Gunnet J., Look R., Ericson E., Murray W.V., Rybczynski P.J., and Zhang X. Bioorg. Med. Chem. Lett. 13 (2003) 4031-4034
6. HIV-1 reverse transcriptase inhibitor:. Santo R.D., and Costi R. IL Farmaco 60 (2005) 385-392
7. Piperidine (1 mL/mmol) in PhMe or pyridine (15 mL/mmol) under reflux:. Pant S., Sharma A., Sharma S.K., Pant U.C., and Goel A.K. Indian J. Chem. 35B (1996) 794-796
8. Upreti M., Pant S., Dandia A., and Pant U.C. Indian J. Chem. 36B (1997) 1181-1184
9. EtOH-HCl under reflux:. Pant S., Singhal B., Upreti M., and Pant U. Molecules 3 (1998) 159-163
10. HOAc in DMF or EtOH at 60 °C for 17 h:. Micheli F., Degiorgis F., Feriani A., Paio A., Pozzan A., Zarantonello P., and Seneci P. J. Comb. Chem. 3 (2001) 224-228
11. HOAc or TFA (1 mL/mmol) in EtOH or PhMe under reflux:. Lévai A. Heterocycl. Commun. 8 (2002) 375-380
12. Lévai A. Heterocycl. Commun. 8 (2002) 227-232
13. Lévai A. J. Heterocycl. Chem. 41 (2004) 399-403
14. HOAc (3 mL/mmol) in DMF under microwave irradiation:. Patel V.M., and Desai K.R. Indian J. Chem. B (2004) 199-201
15. Inorganic supports (2 g/mmol) at 80 °C:. Kodomari M., Noguchi T., and Aoyama T. Synth. Commun. 34 (2004) 1783-1790
16. 2 in DCE under reflux:. Khatik G.L., Kumar R., and Chakraborti A.K. Synthesis (2007) 541-546
17. 2 in MeOH under reflux:. Khatik G.L., Sharma G., Kumar R., and Chakraborti A.K. Tetrahedron 63 (2007) 1200-1210
18. For a review see:. Lévai A. J. Heterocycl. Chem. 37 (2000) 199-214 and the references cited therein
19. Tundo P., Anastas P., Black D.S., Breen J., Collins T., Memoli S., Miyamoto J., Polyakoff M., and Tumas W. Pure Appl. Chem. 72 (2000) 1207-1228
20. Otto S., and Engberts J.B.F.N. Pure Appl. Chem. 72 (2000) 1365-1372
21. Ribe S., and Wipf P. Chem. Commun. (2001) 299-307
22. Engberts J.B.F.N., and Blandamer M.J. Chem. Commun. (2001) 1701-1708
23. Otto S., and Engberts J.B.F.N. Org. Biomol. Chem. 1 (2003) 2809-2820
24. Li C.-J. Chem. Rev. 105 (2005) 3095-3165
25. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed 44 (2005) 3275-3279
26. Li C.-J., and Chen L. Chem. Soc. Rev. 35 (2006) 68-82
27. Lindström U.M., and Andersson F. Angew. Chem., Int. Ed 45 (2006) 548-551
28. Hailes H.C. Org. Proc. Res. Dev. 11 (2007) 114-120
29. Khatik G.L., Kumar R., and Chakraborti A.K. Org. Lett. 8 (2006) 2433-2436
30. Chankeshwara S.V., and Chakraborti A.K. Org. Lett. 8 (2006) 3259-3262
31. Chakraborti A.K., Rudrawar S., Jadhav K.B., Kaur G., and Chankeshwara S.V. Green Chem. 9 (2007) 1335-1340
32. Mase N., Watanabe K., Yoda H., Takabe K., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 4966-4967
33. Breslow R. Acc. Chem. Res. 24 (1991) 159-164
34. Manabe K., Sun X.M., and Kobayashi S. J. Am. Chem. Soc. 123 (2001) 10101-10102
35. Bhagat S., Sharma R., Sawant D.M., Sharma L., and Chakraborti A.K. J. Mol. Catal. A: Chem. 244 (2006) 20-24
36. Bhagat S., Sharma R., and Chakraborti A.K. J. Mol. Catal. A: Chem. 260 (2006) 235-240
37. Cogolli P., Maiolo F., Testaferri L., Tingoli M., and Tiecco M. J. Org. Chem. 44 (1979) 2642-2646
38. Cogolli P., Maiolo F., Testaferri L., Tingoli M., and Tiecco M. J. Org. Chem. 44 (1979) 2636-2642
39. Hwu J.R., Wong F.F., and Shiao M.-J. J. Org. Chem. 57 (1992) 5254-5255
40. Shiao M.-J., Lai L.-L., Ku W.-S., Lin P.-Y., and Hwu J.R. J. Org. Chem. 58 (1993) 4742-4744
41. Hilhorst E., Chen T.B.R.A., Iskander A.S., and Pandit U.K. Tetrahedron 50 (1994) 7837-7848
42. Surdhar P.S., and Armstrong D.A. J. Phys. Chem. 90 (1986) 5915-5917
43. Ashby E.C., Park W.-S., Goel A.B., and Su W.Y. J. Org. Chem. 50 (1985) 5184-5193
44. Gavande N.S., Kundu S., Badgujar N.S., Kaur G., and Chakraborti A.K. Tetrahedron 62 (2006) 4201-4204
45. Chakraborti A.K., Sharma L., and Nayak M.K. J. Org. Chem. 67 (2002) 6406-6414
46. Chakraborti A.K., Sharma L., and Nayak M.K. J. Org. Chem. 67 (2002) 2541-2547
47. Chakraborti A.K., Nayak M.K., and Sharma L. J. Org. Chem. 67 (2002) 1776-1780
48. Nayak M.K., and Chakraborti A.K. Tetrahedron Lett. 38 (1997) 8749-8752
49. Pinchart A., Dallaire C., Bierbeek A.V., and Gingras M. Tetrahedron Lett. 40 (1999) 5479-5482
50. 2O (4 mg, 0.1 mmol, 10 mol %) under magnetic stirring for 35 min at rt (∼25-30 °C) followed by addition of 4-methylbenzaldehyde (0.12 g, 1 mmol, 1 equiv). The mixture was stirred magnetically until complete consumption of the starting materials (35 min, GCMS). After completion of the reaction, a yellow precipitate was formed and this served as an indicator for monitoring the reaction visually.
51. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed 44 (2005) 3275-3279
52. Klijn J.E., and Engberts J.B.F.N. Nature 435 (2005) 746-747