Synthesis of functionalized benzofurans by a double heck reaction of 2,3-dibromofurans and subsequent 6-electrocyclization/dehydrogenation

Synthesis

Volumn , Issue 14, 2011, Pages 2208-2214

  Salman, Ghazwan Ali ^a   Ali, Asad ^a,b   Hussain, Munawar ^a   Khera, Rasheed Ahmad ^a,c   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b University of Mardan   (Pakistan)

^c UNIVERSITY OF FAISALABAD   (Pakistan)

Author keywords

catalysis; electrocyclization; furans; Heck reaction; palladium

Indexed keywords

ALKENYL; BENZOFURANS; ELECTROCYCLIZATION; FUNCTIONALIZED; FURANS; HECK REACTIONS;

AROMATIC COMPOUNDS; ORGANIC POLLUTANTS;

SYNTHESIS (CHEMICAL);

2 ETHYL 5,6 BIS(6 METHYLHEPTYL)BENZOFURAN 2,5,6 TRICARBOXYLATE; 2 ETHYL 5,6 DIHEXYLBENZOFURAN 2,5,6 TRICARBOXYLATE; 2 ETHYL 5,6 DIISOBUTYLBENZOFURAN 2,5,6 TRICARBOXYLATE; 2 ETHYL 5,6 DIMETHYLBENZOFURAN 2,5,6 TRICARBOXYLATE; 2,3 BIS(4 METHOXYSTYRYL)FURAN; 2,3 BIS(4 METHYLSTYRYL)FURAN; 2,3 BIS(4 TERT BUTOXYSTYRYL)FURAN; 5,6 DIBUTYL 2 ETHYLBENZOFURAN 2,5,6 TRICARBOXYLATE; BENZOFURAN DERIVATIVE; BIS(6 METHYLHEPTYL) 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DI TERT BUTYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DI TERT BUTYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIBUTYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DIBUTYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIBUTYLBENZOFURAN 5,6 DICARBOXYLATE; DIETHYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DIETHYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIETHYLBENZOFURAN 5,6 DICARBOXYLATE; DIHEXYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DIHEXYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIISOBUTYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DIISOBUTYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIISOBUTYLBENZOFURAN 5,6 DICARBOXYLATE; DIMETHYL 3,3' (FURAN 2,3 DIYL)DIACRYLATE; DIMETHYL 3,3' [5 (ETHOXYCARBONYL)FURAN 2,3 DIYL]DIACRYLATE; DIMETHYLBENZOFURAN 5,6 DICARBOXYLATE; ETHYL 4,5 BIS(4 CHLOROSTYRYL)FURAN 2 CARBOXYLATE; FURAN DERIVATIVE; TRIETHYLBENZOFURAN 2,5,6 TRICARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CYCLIZATION; DEHYDROGENATION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION;

EID: 79960150091     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260666     Document Type: Article

References (38)

1. Miyata O, Takeda N, Morikami Y, Naito T, Org. Biomol. Chem. 2003 1 254
2. Xie X, Chen B, Lu J, Han J, She X, Pan X, Tetrahedron Lett. 2004 45 6235
3. Zhang H, Ferreira E M., Stoltz B M., Angew. Chem. Int. Ed. 2004 43 6144
4. Hagiwara H, Sato K, Nishino D, Hoshi T, Suzuki T, Ando M, J. Chem. Soc., Perkin Trans. 1 2001 2946
5. Butin A V., Gutnow A V., Abaev V T., Krapivin G D., Molecules 1999 4 52
6. Fuerst D E., Stoltz B M., Wood J L., Org. Lett. 2000 2 3521
7. Schneider B, Phytochemistry 2003 64 459
8. Katritzky A R., Kirichenkok K, Ji Y, Steel P J., Karelson M, ARKIVOC 2003 (vi) 49
9. Wendt B, Ha H R., Hesse M, Helv. Chim. Acta 2002 85 2990
10. Carlsson B, Singh B N., Temciuc M, Nilsson S, Li Y L., Mellin C, Malm J, J. Med. Chem. 2002 45 623; and references cited therein
11. Kwiecien H, Baumann E, J. Heterocycl. Chem. 1997 34 1587
12. Larock R C., Harrison L W., J. Am. Chem. Soc. 1984 106 4218
13. Mátyus P, Varga I, Rettegi T, Simay A, Kállay N, Károlyházy L, Kocsis A, Varró A, Pénzes I, Papp J G., Curr. Med. Chem. 2004 11 61
14. Wong H N. C., Yu P, Yick C.-Y, Pure Appl. Chem. 1999 71 1041
15. For longicaudatin, see
16. Joshi A S., Li X.-C, Nimrod A C., ElSohly H N., Walker L A., Clark A M., Planta Med. 2001 67 186
17. Sigstad E, Catalan C A. N., Diaz J G., Herz W, Phytochemistry 1993 33 165
18. Drewes S E., Hudson N A., Bates R B., J. Chem. Soc., Perkin Trans. 1 1987 2809
19. For sessiliflorol A, see
20. Chan J A., Shultis E A., Carr S A., DeBrosse C W., Eggleston D S., J. Org. Chem. 1989 54 2098
21. Marston A, Zagorski M G., Hostettmann K, Helv. Chim. Acta 1988 71 1210
22. Drewes S E., Hudson N A., Bates R B., Linz G S., Tetrahedron Lett. 1984 25 105
23. Subrahmanyam K, Rao J M., Vemuri V S. S., Babu S S., Roy C P., Rao K V. J., Indian J. Chem., Sect. B 1982 21 895
24. Seo E.-K, Wall M E., Wani M C., Navarro H, Mukherjee R, Farnsworth N R., Kinghorn A D., Phytochemistry 1999 52 669
25. Seo E.-K, Wani M C., Wall M E., Navarro H, Mukherjee R, Farnsworth N R., Kinghorn A D., Phytochemistry 2000 55 35
26. For piperaduncin B, see ref. 3a and:, Bohlmann F, Zdero C, Chem. Ber. 1976 109 1436
27. For reviews of cross-coupling reactions of polyhalogenated heterocycles, see:, Schröter S, Stock C, Bach T, Tetrahedron 2005 61 2245
28. Schnürch M, Flasik R, Khan A F., Spina M, Mihovilovic M D., Stanetty P, Eur. J. Org. Chem. 2006 3283
29. Dang T T., Ahmad R, Dang T T., Reinke H, Langer P, Tetrahedron Lett. 2008 49 1698
30. Dang T T., Villinger A, Langer P, Adv. Synth. Catal. 2008 350 2109
31. Dang T T., Dang T T., Rasool N, Villinger A, Langer P, Adv. Synth. Catal. 2009 351 1595
32. Bach T, Krüger L, Tetrahedron Lett. 1998 39 1729
33. Bach T, Krüger L, Eur. J. Org. Chem. 1999 2045
34. Bach T, Krüger L, Synlett 1998 1185
35. deMeijere and co-workers reported twofold Heck reactions of 1,2-dibromocycloalk-1-enes and related substrates and subsequent 6-electrocyclization; see:, Voigt K, vonZezschwitz P, Rosauer K, Lansky A, Adams A, Reiser O, deMeijere A, Eur. J. Org. Chem. 1998 1521; and references cited therein
36. Hussain M, Nguyen T H., Langer P, Tetrahedron Lett. 2009 50 3929
37. TenghoToguem S.-M, Hussain M, Malik I, Villinger A, Langer P, Tetrahedron Lett. 2009 50 4962
38. Billingsley K, Buchwald S L., J. Am. Chem. Soc. 2007 129 3358; and references cited therein