A convenient preparation of furo[2,3-b]indoles by conjugated addition of organomagnesium reagents to 2-hydroxyindolylidenemalonates

Tetrahedron

Volumn 59, Issue 16, 2003, Pages 2843-2853

  Morales Ríos, Martha S ^a   Santos Sánchez, Norma F ^a   Fragoso Vázquez, M Jonathan ^a,b   Alagille, David ^a   Villagómez Ibarra, J Roberto ^b   Joseph Nathan, Pedro ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

Author keywords

Chelate controlled conjugated Grignard addition; Furo 2,3 b indoles; Indolylidenecyanoacetates; Indolylidenemalonates; X ray analysis

Indexed keywords

ACETIC ACID DERIVATIVE; AROMATIC COMPOUND; INDOLE DERIVATIVE; MAGNESIUM; MALONIC ACID DERIVATIVE; ORGANOMAGNESIUM; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHELATION; CONJUGATION; GRIGNARD REACTION; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037437131     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00336-3     Document Type: Article

References (31)

1. (a) Joule J.A. Saxtone J.E. Indoles Part IV: The Monoterpenoid Indole Alkaloids; Wiley, New York, 1983;244-259.
2. (b) Salway A.H. J. Chem. Soc. 99:1911;2148-2159
3. (c) Robinson, B. J. Chem. Soc. 1964, 1503.
4. (d) Bohrmann H., Lau-Cam C., Tashiro J., Youngken H.W. Jr. Phytochemistry. 8:1969;645-652.
5. Morales-Ríos M.S., Suárez-Castillo O.R., Joseph-Nathan P. Trends Heterocycl. Chem. 6:1999;111-124.
6. Morales-Ríos M.S., Bucio M.A., Joseph-Nathan P. Tetrahedron. 52:1996;5339-5348.
7. (a) Suárez-Castillo O.R., García-Velgara M., Morales-Ríos M.S., Joseph-Nathan P. Can. J. Chem. 75:1997;959-964.
8. (b) Morales-Ríos M.S., Suárez-Castillo O.R., Joseph-Nathan P. J. Chem. Soc., Perkin Trans. 2. 2000;769-775.
9. Perlmutter P. Conjugated Addition Reactions in Organic Synthesis. 1992;Pergamon, Oxford.
10. (a) Fleming F.F., Wang Q., Zhang Z., Steward O.W. J. Org. Chem. 67:2002;5953-5956.
11. (b) Fleming F.F., Wang Q., Steward W. Org. Lett. 2:2000;1477-1479.
12. (a) Cardillo G., Gentilucci L., Tolomelli A., Tomasini C. Tetrahedron. 55:1999;6231-6242.
13. (b) Fang C., Ogawa T., Suemune H., Sakai K. Tetrahedron: Asymmetry. 2:1991;389-398.
14. (a) Morales-Ríos M.S., Suárez-Castillo O.R., Joseph-Nathan P. J. Org. Chem. 64:1999;1086-1087.
15. (b) Morales-Ríos M.S., Suárez-Castillo O.R., Trujillo-Serrato J.J., Joseph-Nathan P. J. Org. Chem. 66:2001;1186-1192.
16. (c) Morales-Ríos M.S., Santos-Sánchez N.F., Joseph-Nathan P. J. Nat. Prod. 65:2002;136-141.
17. (d) Morales-Ríos M.S., Suárez-Castillo O.R., Joseph-Nathan P. Tetrahedron. 58:2002;1479-1484.
18. (a) Rozhkov V.S., Smushkevich Y.I., Suvorov N.N. Khim. Geterotsikl. Soedin. 1980;55-58. Chem. Abstr. 1980, 93, 8124j.
19. (b) Gibe R., Kerr M.A. J. Org. Chem. 67:2002;6247-6249.
20. Morales-Ríos M.S., Santos-Sánchez N.F., Suárez-Castillo O.R., Joseph-Nathan P. J. Org. Chem. 68:2003;305-311.
21. Burket U., Allinger N.L. ACS Monograph 177. ACS Monograph 177. 1983;American Chemical Society, Washington, DC.
22. (a) Yamada S., Noguchi E. Tetrahedron Lett. 42:2001;3621-3624.
23. (b) Derrick S.D., Boehme R., Wong K.M., Nemeth F., Tanaka K., Rumberg B., Beekman R.A., Dibbe P.W. Tetrahedron. 52:1996;7679-7690.
24. (c) Harrison D.M. Tetrahedron Lett. 25:1984;6063-6064.
25. (d) Rees C.W., Sabet C.R. J. Chem. Soc. 1965;870-875.
26. (e) Buchardt O., Lohse C. Tetrahedron Lett. 1966;4355-4361.
27. (a) Morales-Ríos M.S., García-Velgara M., Cervantes-Cuevas H., Alvarez-Cisneros C., Joseph-Nathan P. Magn. Reson. Chem. 38:2000;172-176.
28. (b) Morales-Ríos M.S., Suárez-Castillo O.R., Alvarez-Cisneros C., Joseph-Nathan P. Can. J. Chem. 77:1999;130-137.
29. (c) Morales-Ríos M.S., Mora-Pérez Y., Joseph-Nathan P. Magn. Reson. Chem. 30:1992;1153-1157.
30. Schut, R. N.; Safdy, M. E.; Hong, E. US Patent 4,283,410, August 11, 1981.
31. 2=10.3%, GOF=0.954. CCDC deposition number 204989.