Palladium-Catalyzed Synthesis of Lipophilic Benzo[b]furans from Cardanol

Roberta Bernini; Sandro Cacchi; Ilse De Salve; Giancarlo Fabrizi

doi:10.1055/s-2007-965939

PAPER

Palladium-Catalyzed Synthesis of Lipophilic Benzo[b]furans from Cardanol

Roberta Bernini^a, Sandro Cacchi*^b, Ilse De Salve^a, Giancarlo Fabrizi*^b
^a Dipartimento A.B.A.C., Università degli Studi della Tuscia, Via S. Camillo De Lellis, 01100 Viterbo, Italy
^b Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi ‘La Sapienza’, P. le A. Moro 5, 00185 Rome, Italy
Fax: +39(06)49912795; e-Mail: sandro.cacchi@uniroma1.it;

Abstract

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Abstract

o-Iodocardanol, readily available from cardanol by iodination, has been used to prepare a variety of lipophilic benzo[b]furans. 2-Substituted benzo[b]furans have been prepared by a Sonogashira cross-coupling/cyclization process. 2,3-Disubstituted benzo[b]furans have been obtained from o-alkynylcardanols by an oxypalladation/reductive elimination process.

Key words

cross-coupling - cyclization - alkynes - benzo[b]furans - catalysis

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References

1 Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003, 103: 893

2a Judd DB. Dowle MD. Middlemiss D. Scopes DLC. Ross BC. Jack TL. Pass M. Tranquillini E. Hobson JE. Panchal TA. Stuart PG. Paton JMS. Hubbard T. Hilditch A. Drew GM. Robertson MJ. Clark KL. Travers A. Hunt AAE. Polley J. Eddershaw PJ. Bayliss MK. Manchee GR. Donnelly MD. Walker DG. Richards SA. J. Med. Chem. 1994, 37: 3108

2b Kiyama R. Homna T. Hayashi K. Ogawa M. Hara M. Fujimoto M. Fujishita T. J. Med. Chem. 1995, 38: 2728

2c Yoo S. Kim S.-K. Lee S.-H. Kim N.-J. Lee D.-W. Bioorg. Med. Chem. 2000, 8: 2311

3a Gangjee A. Devraj R. McGuire JJ. Kisliuk RL. J. Med. Chem. 1995, 38: 3798

3b Gangjee A. Devraj R. McGuire JJ. Kisliuk RL. J. Med. Chem. 1995, 38: 4495

3c Hennequin LFA. inventors; WO 2003047585. ; Chem. Abstr. 2003, 139, 36448

3d Helesbeux JJ. Duval O. Seraphin D. Roussakis C. Richomme P. J. Enzyme Inhib. Med. Chem. 2003, 18: 159

3e Hayakawa I. Shioya R. Agatsuma T. Furukawa H. Sugano Y. Bioorg. Med. Chem. Lett. 2004, 14: 3411

3f Eberle M, Bachmann F, Strebel A, Roy S, Saha G, Sadhukhan SK, Saxena R, and Srivastava S. inventors; WO 2005061476. ; Chem. Abstr. 2005, 143, 115430

3g Rida SM. El-Hawash SAM. Fahmy HTY. Hazza AA. El-Meligy MMM. Arch. Pharm. Res. 2006, 29: 16

4a Gubin J. de Vogelaer H. Inion H. Houben C. Lucchetti J. Mahaux J. Rosseels G. Peiren M. Clinet M. Polster P. Chatelain P. J. Med. Chem. 1993, 36: 1425

4b Kozikowsky AP. Ma D. Du L. Lewin NE. Blumberg PM. Farmaco 1995, 50: 425

4c Kozikowsky AP. Ma D. Du L. Lewin NE. Blumberg PM. J. Am. Chem. Soc. 1995, 117: 6666

4d Termin AP, Martinborough E, Zimmermann N, Cohen CJ, and Gutierrez CD. inventors; WO 2006010008. ; Chem. Abstr. 2006, 144, 164278

5 Ohemeng KA. Apollina MA. Nguyen VN. Schwender CF. Singer M. Steber M. Ariseli J. Argentieri D. Hageman W. J. Med. Chem. 1994, 37: 3663

6a Nagahara T. Yokoyama Y. Inamura K. Katakura S. Komoriya S. Yamaguchi H. Rara T. Iwamoto M. J. Med. Chem. 1994, 37: 1200

6b Kawaguchi T, Akatsuka H, Iijima T, Tsuboi Y, Mitsui T, and Murakami J. inventors; WO 2003082847. ; Chem. Abstr. 2003, 139, 292142

7 Boschelli DH. Bramer JB. Khtana SS. Sorenson RJ. Connor DT. Ferin MA. Wright CD. Lesch ME. Imre K. Okonkwo GC. Schrier DJ. Conroy MC. Ferguson E. Woelle J. Saxena U. J. Med. Chem. 1995, 38: 4597

8a Yang Z. Liu HB. Lee CM. Chang HM. Wong HNC. J. Org. Chem. 1992, 57: 7248

8b Kuo Y.-H. Wu C.-H. J. Nat. Prod. 1996, 59: 625

9 Lu J, Ma T, Nagpal S, Shen Q, Warshawsky AM, Ochoada JM, and Yee YK. inventors; WO 2005051938. ; Chem. Abstr. 2005, 143, 43763

10 Frangin G, and Malik M. inventors; WO 9840067. ; Chem. Abstr. 1998, 129: 239887

11a Jinno S. Okita T. Inouye K. Bioorg. Med. Chem. Lett. 1999, 9: 1029

11b Varvaresou A. Iakovou K. Filippatos E. Souli C. Calogeropoulou T. Ioannidou I. Kourounakis AP. Pannecouque C. Witvrouw M. Padalko E. Neyts J. De Clercq E. Tsotinis A. Arzneim.-Forsch. 2001, 51: 156

12 Johansson G, Brandt P, and Nilsson BM. inventors; WO 2005058858. ; Chem. Abstr. 2005, 143, 97253

13a Ohemeng KA. Appollina MA. Nguyen VN. Schwender CF. Singer M. Steber M. Ansell J. Argentieri D. Hageman W. J. Med. Chem. 1994, 37: 3663

13b Ecker G. Chiba P. Hitzler M. Schmid D. Visser K. Cordes HP. Csoellei J. Seydel JK. Schaper K.-J. J. Med. Chem. 1996, 39: 4767

13c Ashwood VA. Field MJ. Horwell DC. Julien-Larose C. Lewthwaite RA. McCleary S. Pritchard MC. Raphy J. Singh L. J. Med. Chem. 2001, 44: 2276

13d Murthy VS. Kulkarni VM. Bioorg. Med. Chem. 2002, 10: 2267

13e Collini MD. Kaufman DH. Manas ES. Harris HA. Henderson RA. Xu ZB. Unwalla RJ. Miller CP. Bioorg. Med. Chem. Lett. 2004, 14: 4925

14a Arcadi A. Marinelli F. Cacchi S. Synthesis 1986, 749

14b Arcadi A. Cacchi S. Del Rosario M. Fabrizi G. Marinelli F. J. Org. Chem. 1996, 61: 9280

For a recent review on the palladium-catalyzed construction and functionalization of benzo[b]furans, see:

14c Cacchi S. Fabrizi G. Goggiamani A. Curr. Org. Chem. 2006, 10: 1423

For reviews on the chemistry of cardanol, see:

15a Tyman JHP. Chem. Soc. Rev. 1979, 8: 499

15b Attanasi OA. Buratti S. Filippone P. Chim. Ind. (Milan) 1996, 78: 693

16 Hu Y. Nawoschik KJ. Ma J. Fathi R. Yang Z. J. Org. Chem. 2004, 69: 2235

17 Arcadi A. Attanasi OA. Berretta S. Bianchi G. Filippone P. Synthesis 2006, 2523

For some recent references, see:

18a Genin E. Amengual R. Michelet V. Savignac M. Jutand A. Neuville L. Genet J.-P. Adv. Synth. Catal. 2004, 346: 1733

18b Liang B. Dai M. Chen J. Yang Z. J. Org. Chem. 2005, 70: 391

18c Liang B. Huang M. You Z. Xiong Z. Lu K. Fathi R. Chen J. Yang Z. J. Org. Chem. 2005, 70: 6097

18d Ohshita J. Nada D. Tada Y. Kimura Y. Yoshida H. Kunai A. Kunugi Y. J. Organomet. Chem. 2005, 690: 3951

18e Batchu VR. Subramanian V. Parasuraman K. Swamy NK. Kumar S. Pal M. Tetrahedron 2005, 61: 9869

18f Anderson KW. Buchwald SL. Angew. Chem. Int. Ed. 2005, 44: 6173

18g Gil-Molto J. Karlstroem S. Najera C. Tetrahedron 2005, 61: 12168

18h Tremblay-Morin J.-P. Ali H. van Lier JE. Tetrahedron Lett. 2005, 46: 6999

18i Xue C. Luo F.-T. Chen J. Liu H. Anal. Chim. Acta 2006, 569: 27

18j Corma A. Garcia H. Primo A. J. Catal. 2006, 241: 123

18k Li Y. Zhou P. Dai Z. Hu Z. Sun P. Bao J. New J. Chem. 2006, 30: 832

18l Ali H. St-Jean O. Tremblay-Morin J.-P. van Lier JE. Tetrahedron Lett. 2006, 47: 8275

19 Songashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 50: 4467