Captodative olefins: Methyl 2-aryloxy-3-dimethyl-aminopropenoates and their application in a new synthesis of benzofurans

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2377-2380

  Cruz, María Del Carmen ^a   Tamariz, Joaquín ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

Author keywords

2 Aryloxy 3 dimethylaminopropenoates; Benzofurans; Captodative olefins; Cyclization; Lewis acid catalysis

Indexed keywords

ALKENE DERIVATIVE; BENZOFURAN DERIVATIVE; ESTER DERIVATIVE; LEWIS ACID; PROPANOLAMINE DERIVATIVE;

AMINOMETHYLENATION; ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 1242270585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.073     Document Type: Article

References (46)

1. Cagniant P., Cagniant D. Recent Advances in the Chemistry of Benzo[b]furan and Its Derivatives. Part I: Occurrence and Synthesis. Adv. Heterocycl. Chem. 18:1975;337-482.
2. Bird C.W., Cheeseman G.W.H. Synthesis of Five-membered Rings with One Heteroatom. Katritzky A.R. Comprehensive Heterocyclic Chemistry. Vol. 4:1984;89-153 Pergamon, New York.
3. Donelly D.M.X., Meegan M.J. Furans and Their Benzo Derivatives: (iii) Synthesis and Applications. Katritzky A.R. Comprehensive Heterocyclic Chemistry. Vol. 4:1984;657-712 Pergamon, New York.
4. For recent examples, see: Stevenson P.C., Simmonds M.S.J., Yule M.A., Veitch N.C., Kite G.C., Irwin D., Legg M. Phytochemistry. 63:2003;41-46.
5. Tanaka H., Oh-Uchi T., Etoh H., Sako M., Sato M., Fukai T., Teteishi Y. Phytochemistry. 63:2003;597-602.
6. Ali Z., Tanaka T., Iliya I., Iinuma M., Furusawa M., Ito T., Nakaya K.-I., Murata J., Darnaedi D. J. Nat. Prod. 66:2003;558-560.
7. Wyatt P.G., Allen M.J., Chilcott J., Gardner C.J., Livermore D.G., Mordaunt J.E., Nerozzi F., Patel M., Perren M.J., Weingarten G.G., Shabbir S., Woollard P.M., Zhou P. Bioorg. Med. Chem. Lett. 12:2002;1405-1411.
8. Malamas M.S., Sredy J., Moxham C., Katz A., Xu W., McDevitt R., Adebayo F.O., Sawicki D.R., Seestaller L., Sullivan D., Taylor J.R. J. Med. Chem. 43:2000;1293-1310.
9. Huang H.-C., Chamberlain T.S., Seibert K., Koboldt C.M., Isakson P.C., Reitz D.B. Bioorg. Med. Chem. Lett. 5:1995;2377-2380.
10. 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. 36:1993;1425-1433.
11. Novák Z., Timári G., Kotschy A. Tetrahedron. 59:2003;7509-7513.
12. Bishop B.C., Cottrell I.F., Hands D. Synthesis. 1997;1315-1320.
13. Larock R.C., Yum E.K., Doty M.J., Sham K.K.C. J. Org. Chem. 60:1995;3270-3271.
14. Hiroya K., Hashimura K., Ogasawara K. Heterocycles. 38:1994;2463-2472.
15. Satoh M., Miyaura N., Suzuki A. Synthesis. 1987;373-377.
16. de Souza N.J., Nayak P.V., Secco E. J. Heterocycl. Chem. 3:1966;42-45.
17. Bosch J., Roca T., Catena J.-L., Farrerons C., Miquel I. Synthesis. 2000;721-725.
18. Hellwinkel D., Göke K. Synthesis. 1995;1135-1141.
19. Fürstner A., Jumbam D.N. Tetrahedron. 48:1992;5991-6010.
20. Burke J.M., Stevenson R. J. Chem. Res. (S). 1985;34.
21. Elliott E.D. J. Am. Chem. Soc. 73:1951;754.
22. Gardiner M., Grigg R., Sriharan V., Vicker N. Tetrahedron Lett. 39:1998;435-438.
23. Beckwith A.L.J., Meijs G.F. J. Chem. Soc., Chem. Commun. 1981;136-137.
24. Spagnolo P., Tiecco M., Tundo A., Martelli G. J. Chem. Soc., Perkin Trans. 1. 1972;556-559.
25. MacLeod J.K., Worth B.R. Tetrahedron Lett. 1972;237-240.
26. Royer R., René L. Bull. Soc. Chim. Fr. 1970;1037-1040.
27. Elvidge J.A., Foster R.G. J. Chem. Soc. 1964;981-991.
28. Herrera R., Jiménez-Vázquez H.A., Modelli A., Jones D., Söderberg B.C., Tamariz J. Eur. J. Org. Chem. 2001;4657-4669.
29. Reyes A., Aguilar R., Muñoz A.H., Zwick J.-C., Rubio M., Escobar J.-L., Soriano M., Toscano R., Tamariz J. J. Org. Chem. 55:1990;1024-1034. and references included therein.
30. Jiménez-Vázquez H.A., Ochoa M.E., Zepeda G., Modelli A., Jones D., Mendoza J.A., Tamariz J. J. Phys. Chem. A. 101:1997;10082-10089.
31. Peralta J., Bullock J.P., Bates R.W., Bott S., Zepeda G., Tamariz J. Tetrahedron. 51:1995;3979-3996.
32. In particular, enaminones have proved to be privileged Michael acceptors: Lue P., Greenhill J.V. Enaminones in Heterocyclic Synthesis. Adv. Heterocycl. Chem. 67:1997;207-343.
33. Elassar A.-Z.A., El-Khair A.A. Tetrahedron. 59:2003;8463-8480.
34. Stanovnik B., Svete J. Synlett. 2000;1077-1091.
35. Greenhill J.V. Chem. Soc. Rev. 6:1977;277-294.
36. Mendoza J.A., Jiménez-Vázquez H.A., Herrera R., Liu J., Tamariz J. Rev. Soc. Quím. Méx. 47:2003;116-208.
37. Aguilar, J. R. M.Sc. Thesis, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, 2000.
38. 5: C, 59.91; H, 6.81. Found: C, 60.02; H, 6.95.
39. For a related synthesis of 3-dimethylaminopropenoates, see: Smodis J., Stanovnik B. Tetrahedron. 54:1998;9799-9810.
40. Selic L., Grdadolnik S.G., Stanovnik B. Helv. Chim. Acta. 80:1997;2418-2425.
41. Grdadolnik S.G., Stanovnik B. Magn. Reson. Chem. 35:1997;482-486.
42. Labarrios F., Garduño L., Vidal M.R., García R., Salazar M., Martínez E., Díaz F., Chamorro G., Tamariz J. J. Pharm. Pharmacol. 51:1999;1-7.
43. 5: C, 58.40; H, 6.24. Found: C, 58.48; H, 6.14.
44. Olah G.A., Krishnamurti R., Prakash G.K.S. Friedel-Crafts Alkylations. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;293-339 Pergamon, Oxford.
45. Mahindaratne M.P.D., Wimalasena K. J. Org. Chem. 63:1998;2858-2866.
46. 5: C, 61.02; H, 5.12. Found: C, 61.07; H, 5.39.