Palladium mediated stereospecific synthesis of 3-enynyl substituted thioflavones/flavones

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2305-2309

  Pal, Manojit ^a   Parasuraman, Karuppasamy ^a   Subramanian, Venkataraman ^a   Dakarapu, Rambabu ^a   Yeleswarapu, Koteswar Rao ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

3 Enynyl alkynyl thioflavones; 3 Iodo(thio)flavone; Palladium catalyst; Stereocontrolled synthesis

Indexed keywords

3 IODO(THIO)FLAVONE; ALKENE DERIVATIVE; ALKENYL GROUP; COPPER DERIVATIVE; FLAVONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HECK REACTION; SONOGASHIRA REACTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 1242293079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.113     Document Type: Article

References (50)

1. Khattab A.M., Grace M.H., El-Khrisy E.A. Pharmazie. 56:2001;661.
2. Nohara A., Umetani T., Sanno Y. Tetrahedron. 30:1974;3553. and references cited therein.
3. Horie T., Tominaga H., Kawamura Y., Hada T., Ueda N., Amano Y., Yamamoto S. J. Med. Chem. 34:1991;2169.
4. For 2,3-diarylflavone as a COX-2 inhibitor, see: Joo Y.H., Kim J.K., Kang S.-H., Noh M.-S., Ha J.-Y., Choi J.K., Lim K.M., Lee C.H., Chung S. Bioorg. Med. Chem. Lett. 13:2003;413.
5. ven Acker F.A.A., Hageman J.A., Haenen G.R.M.M., van der Vijgh W.J.F., Bast A., Menge W.M.P.B. J. Med. Chem. 43:2000;3752.
6. Konishi M., Ohkuma H., Matsumoto K., Tsuno T., Kamei H., Miyake T., Oki T., Kawaguchi H., Van Duyne G.D., Clardy J. J. Antibiot. 42:1989;1449.
7. Nussbaumer P., Leitner L., Marz K., Stutz A. J. Med. Chem. 38:1995;1831.
8. Padakanti S., Veeramaneni V.R., Pattabiraman V.R., Pal M., Yeleswarapu K.R. Tetrahedron Lett. 43:2002;8715.
9. Pal M., Rao V.V., Srinivas P., Murali N., Akhila V., Premkumar M., Rao C.S., Misra P., Ramesh M., Rao Y.K. Indian J. Chem. 42B:2003;593.
10. Pal M., Veeramaneni V.R., Nagaballi M., Kalleda S.R., Misra P., Casturi S.R., Yeleswarapu K.R. Bioorg. Med. Chem. Lett. 13:2003;1639.
11. Pal M., Madan M., Srinivas P., Pattabiraman V.R., Kalleda S.R., Akhila V., Ramesh M., Rao Mamidi N.V.S., Casturi S.R., Malde A., Gopalakrishnan B., Yeleswarapu K.R. J. Med. Chem. 46:2003;3975.
12. Pattabiraman V.R., Padakanti P.S., Veeramaneni V.R., Pal M., Yeleswarapu K.R. Synlett. 2002;947.
13. Pal M., Batchu V.R., Khanna S., Yeleswarapu K.R. Tetrahedron. 58:2002;9933.
14. Pal M., Batchu V.R., Parasuraman K., Yeleswarapu K.R. J. Org. Chem. 68:2003;6806.
15. For our earlier synthesis of 3-alkynyl substituted flavones, see: Pal M., Subramanian V., Parasuraman K., Yeleswarapu K.R. Tetrahedron. 59:2003;9563.
16. We postulated that attachment of an enyne moiety at the C-3 position of the (thio)flavone ring may lead to a novel class of compounds of potential biological interest. For biological properties of 6-enynyl substituted flavones, see: Artali R., Barili P.L., Bombieri G., Re P.D., Marchini N., Meneghetti F., Valenti P. Il Farmaco. 58:2003;875.
17. For the synthesis of 3-alkyl/alkenyl flavones, see: Lokshin V., Heynderickx A., Samat A., Pepe G., Guglielmetti R. Tetrahedron Lett. 40:1999;6761.
18. Goyal S., Parthasarathy M.R. Indian J. Chem. 31B:1992;391.
19. For a review, see: Ghosh C.K., Ghosh C. Indian J. Chem. 36B:1997;968.
20. Nakazumi H., Endo T., Sonoda H., Kitao T. J. Heterocycl. Chem. 22:1985;821.
21. Dhara M.G., De S.K., Mallik A.K. Tetrahedron Lett. 37:1996;8001.
22. For synthesis via a Ru-catalyzed reaction, see: Melis K., Samulkiewicz P., Rynkowski J., Verpoort F. Tetrahedron Lett. 43:2002;2713. and references cited therein.
23. For synthesis via a Pd-catalyzed reaction, see: Trost B.M., Chan C., Ruhter G. J. Am. Chem. Soc. 109:1987;3486.
24. Beard R.L., Klein E.S., Standeven A.M., Escobar M., Chandraratna R.A.S. Bioorg. Med. Chem. Lett. 11:2001;765.
25. Thadani A.N., Rawal V.H. Org. Lett. 4:2002;4321.
26. Nuss J.M., Levine B.H., Rennels R.A., Heravi M.M. Tetrahedron Lett. 32:1991;5243.
27. Negishi E., Noda Y., Lamaty F., Vawter E.J. Tetrahedron Lett. 31:1990;4393.
28. Torii S., Okumoto H., Tadokoro T., Nishimura A., Rashid A. Tetrahedron Lett. 34:1993;2139.
29. For synthesis via a Lewis acid-catalyzed reaction, see: Ishikawa T., Aikawa T., Mori Y., Saito S. Org. Lett. 5:2003;51.
30. Heck R.F. J. Am. Chem. Soc. 90:1968;5518.
31. Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467.
32. For an excellent review, see: Meijere A. de, Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379.
33. Pal M., Parasuraman K., Yeleswarapu K.R. Org. Lett. 5:2003;349.
34. Pal M., Parasuraman K., Gupta S., Yeleswarapu K.R. Synlett. 2002;1976.
35. Pal M., Subramanian V., Yeleswarapu K.R. Tetrahedron Lett. 44:2003;8221.
36. Pal M., Kundu N.G. J. Chem. Soc., Perkin Trans. 1. 1996;449.
37. Heteroaryl halides were chosen from those, which contain an enone moiety such as -CO-C(X)=C- (where X=I, Br, Cl) as a part of the heterocyclic ring.
38. This product was detected while monitoring the reaction using TLC where it appeared below the desired product when visualized under UV light.
39. For a similar type of Pd-catalyzed transformation, see: Gonzalez J.J., Francesch A., Cardenas D.J., Echavarren A.M. J. Org. Chem. 63:1998;2854.
40. 3-Iodothioflavone and 3-iodoflavone were prepared according to a known procedure, see: Zhang F.J., Li Y.L. Synthesis. 1993;565.
41. All the terminal alkynes used are commercially available.
42. 2OH), 31.5 (2C, Me), 29.1 (2C, Me).
43. Larock R.C., Tian Q. J. Org. Chem. 63:1998;2002.
44. 4, see: Dang H., Garcia-Garibay M.A. J. Am. Chem. Soc. 123:2001;355.
45. 2 group at C-2, but none between H-1 and the Me (1.36 δ ) at C-5 indicating the syn orientation of the heterocyclic and acetylenic moieties across the double bond.
46. For a discussion on the generation of Pd(0) species from Pd(II) complexes, see: Hegedus L.S. Angew. Chem., Int. Ed. Engl. 27:1988;1113. and references cited therein.
47. -. For a review, see: Amatore C., Jutand A. Acc. Chem. Res. 33:2000;314.
48. Wu M.-J., Wei L.-M., Lin C.-F., Leou S.-P., Wei L.-L. Tetrahedron. 57:2001;7839. See also Ref. 17.
49. The stability of A may be accounted for by the contribution from the following resonance structures.
50. 16a in their study.