Zirconium(IV) chloride catalyzed cyclization of ortho-allylphenols: Synthesis of 2-methyl-2,3-dihydrobenzofurans

Synthetic Communications

Volumn 34, Issue 17, 2004, Pages 3091-3097

  Meshram, H M ^a   Premalatha, K ^a   Rameshbabu, K ^a   Eeshwaraiah, B ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Dihydrobenzofurans; Intramolecular cyclization; ortho Allylphenols; Zirconium (IV) chloride

Indexed keywords

1,2 ALLYLPHENOL; 2 METHYL 2,3 DIHYDROBENZOFURAN; FURAN DERIVATIVE; PHENOL DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; ZIRCONIUM CHLORIDE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; SYNTHESIS;

EID: 5344264442     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200028551     Document Type: Article

References (22)

1. (a) Sih, C.J.; Ravikumar, P.R.; Huang, F.; Buckner, C.; Whitloc, H. Isolation and synthesis of pinoresinol diglucoside, a major antihypertensive principle of Tu Chung (Eucommio uhnoides, oliver). J. Am. Chem. Soc. 1976, 98, 5412;
2. (b) Nagai, M.; Noguchi, M.; Iizuka, T.; Otani, K.; Kamata, K. Vascodilator effects of des(α-carboxy-3,4,dihydroxy phenethy) lithospermic acid (8-epiblechnic acid), a derivative of lithospermic acid in solviac Miltiorrhizae Radix. Biol. Pharm. Bull. 1996, 19, 228-232;
3. (c) Nikaido, T.; Ohmoto, T.; Kinoshita, T.; Sankawa, H.; Nishibe, S.; Hisada, S. Chem. Pharm. Bull. 1981, 29, 3586-3592.
4. (a) Brufani, M.; Ceccarelli, S.; Giannetti, P.; Paesono, A.; Scuri, R.; Zanarella, S Br. Pat. 2221 463 1990;
5. (b) Preparation of (RS)-2-(2,3-dihydro-5-hydroxy-4,6,7- trimethylbenzofuranyl) acetic acid, 2-(2,3-dihydro-5-acyloxy-4,6,7- trimethylbenzofuranyl) acetic acid and their esters. Antihypertensive drugs. Chem. Abstr. 1990, 113, 58915;
6. (c) Brunmer, H. Euro. Pat. Offen. 2227423, s1972;
7. (d) Chem. Abstr. 1973, 78, 62181.
8. (a) Maier, L. Organic phosphorus compounds 68. The direct synthesis of tri (alkyl and aryl seleno) phosphites and of tris(p-anisyltelluro) phosphite (1). Helv. Chim. Acta. 1976, 252;
9. (b) KaraKhanov, E.A.; Freger, A.A.; Viktorova, E.A. Mechanism of phenol synthesis during reactions of 2,3-dihydrobenzofurans on acid catalysts. Izv. Vyssh Vche Zagved Khim. Khim Tekhnol. 1973, 16 (4), 586-588.
10. (a) Cho, J.Y.; Kyong, U.; Baik, K.U.; Yoo, E.S.; Yoshikawa, K.; Park, M.H. In vitro anti-inflammatory effects of neolignonan woorenosides from the rhizomes of Coptis japanica. J. Natl. Prod. 2000, 63, 1205-1209;
11. (b) Laszlo, J.; Laszlo, K.; Sandor, A. Simple synthesis of benzofuranoid neolignane from Myristica fragrans. J. Natl. Prod. 2000, 63, 866-870.
12. Bergman, J.; Engman, L. Oxidatuve cyclization of some γ- and δ-hydroxy olefins indused by telurium dioxide. J. Am. Chem. Soc. 1981, 103, 5196-5200.
13. Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. Palladium-catalyzed carbonylative annulation of -o-alkynyl phenols: synthesis of 2- substitutes- 3-aroyl-benzo(b) furans. J. Org. Chem. 2002, 67, 2365-2368.
14. Evans, D.A.; Chapman, K.T.; Bisaha, J. Asymmetric Diels-Alder cyclo addition reactions with chiral α,β-unsaturated N-acyloxazolidinones. Am. Chem. Soc. 1988, 110, 1238.
15. Yam, V.W.W.; Chong, S.H.F.; Chung, C.K.K. Synthesis and luminescence behaviour of rhenium(I) diynl complexes. X-ray crystal structures of [Re(co)3(tBu2bpy)(C≡C-C≡C-H)] and [Re(Co)3(tBu2bpy) (C≡C-C≡C-ph)]. Chem. Commun. 1998, 19, 2121.
16. Phillipson, N.; Anson, M.S.; Montana, J.G.; Taylor, R.J.K. Ketone homologation to produce α-methoxy ketones: application to conduritol synthesis. J. Chem. Soc. Perkin. Trans. I 1997, 19, 2821.
17. 4-Mediated regioselective electrophilic amination of activated arenes with new alkyl aryl amino carbonyl diazene carboxylates: intermolecular and intramolecular reactions. J. Org. Chem. 1999, 64, 2558.
18. Caminade, A.-M.; Majorl, J.P; Joopknol; Ben, L.F. Phosphorhydrazide macrocycles and cryptands. Synlett. 1996, 11, 1025.
19. Harrowven, D.C.; Dainty, R.F. Zirconium tetrachloride as a mediator for ambient temperature ortho-Fries rearrangements. Tetrahedron Lett. 1996, 37, 7659.
20. 4+-Catalyzed efficient synthesis of α-amino phosphonates. Synthesis 2001, 15, 2277.
21. (a) Yadav, J.S.; Reddy, G.S.; Meshram, H.M. Zinc promoted simple and convenient synthesis of carbomates: an easy access for amino group protection. Tetrahedron Lett. 1998, 39, 3259;
22. (b) Meshram, H.M.; Reddy, G.S.; Reddy, M.M.; Yadav, J.S. Zinc mediated facile amide formation: application to alkyl, aryl, heterocyle, carbohydrate and amino acids. Tetrahedron Lett. 1998, 39, 4103.