A new synthesis of monosubstituted succinaldehydes and 3-substituted pyrroles from acetonitriles. Formal synthesis of 2,3-dihydro-7-methyl-2H-pyrrolizidin-1-one (Danaidone), a semiochemical of Danaid butterflies

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4099-4102

  Méndez, Jose Manuel ^a   Flores, Blas ^a   Léon, Fernando ^a   Martínez, María Eugenia ^a   Vázquez, Alfredo ^a   García, Gustavo Alberto ^a   Salmón, Manuel ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

DANAINAE; PAPILIONOIDEA;

1 (2 CYANOETHYL) 3 METHYLPYRROLE; ACETONITRILE DERIVATIVE; ALDEHYDE DERIVATIVE; DANAIDONE; PYRROLE DERIVATIVE; SUCCINALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0029882264     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00765-4     Document Type: Article

References (21)

1. Sundberg, R.J.; In "Comprehensive Heterocyclic Chemistry", Bird, C.W.; Cheesman, G.W.H.; Eds.; Pergamon Press; Oxford , Vol. 4, Part III, 1984, 313, and references therein.
2. Sakai, K.; Suzuki, M.; Nunami, K.; Yoneda, N.; Onoda, Y.; Iwasawa, Y.; Chem. Pharm Bull. 1980, 28, 2384.
3. Collard, D.M.; Fox, M.A.; J. Am. Chem. Soc. 1991, 113, 9415. Salmón, M.; Saloma, M.; Bidan, G.; Ganies, E.M.; Electrochimica Acta 1989, 34, 117. Andrieux, C.P.; Audebert, P.; Hapiot, P.; Saveant, J.M.; J. Am. Chem. Soc. 1990, 112, 2439. For a review see Curran, D.; Grimshaw, J.; Perera, S. D.; Chem. Soc. Rev. 1991, 20, 391.
4. Collard, D.M.; Fox, M.A.; J. Am. Chem. Soc. 1991, 113, 9415. Salmón, M.; Saloma, M.; Bidan, G.; Ganies, E.M.; Electrochimica Acta 1989, 34, 117. Andrieux, C.P.; Audebert, P.; Hapiot, P.; Saveant, J.M.; J. Am. Chem. Soc. 1990, 112, 2439. For a review see Curran, D.; Grimshaw, J.; Perera, S. D.; Chem. Soc. Rev. 1991, 20, 391.
5. Collard, D.M.; Fox, M.A.; J. Am. Chem. Soc. 1991, 113, 9415. Salmón, M.; Saloma, M.; Bidan, G.; Ganies, E.M.; Electrochimica Acta 1989, 34, 117. Andrieux, C.P.; Audebert, P.; Hapiot, P.; Saveant, J.M.; J. Am. Chem. Soc. 1990, 112, 2439. For a review see Curran, D.; Grimshaw, J.; Perera, S. D.; Chem. Soc. Rev. 1991, 20, 391.
6. Collard, D.M.; Fox, M.A.; J. Am. Chem. Soc. 1991, 113, 9415. Salmón, M.; Saloma, M.; Bidan, G.; Ganies, E.M.; Electrochimica Acta 1989, 34, 117. Andrieux, C.P.; Audebert, P.; Hapiot, P.; Saveant, J.M.; J. Am. Chem. Soc. 1990, 112, 2439. For a review see Curran, D.; Grimshaw, J.; Perera, S. D.; Chem. Soc. Rev. 1991, 20, 391.
7. Jackson, A.H.; In "Pyrroles. Part I. The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring". Jones, R.A., Ed.; John Wiley & Sons, New York, 1990, pp. 295-303.
8. For recent synthesis of β-substituted pyrroles see, Campi, E.M.; Jackson, W.R.; Nilsson, Y.; Tetrahedron Lett. 1991, 32, 1093. Bray, B.L.; Mathies, P.H.; Naef, R.; Solas, D.R.; Tidwell, T.T.; Artis, D.R.; Muchowski, J.M.; J. Org. Chem. 1990, 55, 6317. For a review see, Andersen, H.J.; Loander, C.E.; Synthesis 1985, 353.
9. For recent synthesis of β-substituted pyrroles see, Campi, E.M.; Jackson, W.R.; Nilsson, Y.; Tetrahedron Lett. 1991, 32, 1093. Bray, B.L.; Mathies, P.H.; Naef, R.; Solas, D.R.; Tidwell, T.T.; Artis, D.R.; Muchowski, J.M.; J. Org. Chem. 1990, 55, 6317. For a review see, Andersen, H.J.; Loander, C.E.; Synthesis 1985, 353.
10. For recent synthesis of β-substituted pyrroles see, Campi, E.M.; Jackson, W.R.; Nilsson, Y.; Tetrahedron Lett. 1991, 32, 1093. Bray, B.L.; Mathies, P.H.; Naef, R.; Solas, D.R.; Tidwell, T.T.; Artis, D.R.; Muchowski, J.M.; J. Org. Chem. 1990, 55, 6317. For a review see, Andersen, H.J.; Loander, C.E.; Synthesis 1985, 353.
11. Vázquez, A.; Flores, B.; León, F.; González, A.; García de la Mora, G.; Méndez, J.M.; Fourth Chemical Congress of North America, New York, N.Y., Aug., 25-30, 1991. Abstract ORGN 196.
12. All new compounds were fully characterized by the usual spectroscopic and analytical techniques.
13. If this hydrolysis is conducted at 0°C, the mono acetal of the succinaldehydes can be isolated in good yields.
14. Gilchrist, T.L.; Heterocyclic Chemistry, 2nd. Ed.; Longman Scientific & Technical; Hong Kong, 1992, p. 190.
15. Babler, J.H.; Spina, K.P.; Tetrahedron Lett. 1984, 25, 1659.
16. Larson, G.L.; Klesse, R.; J. Org. Chem. 1985, 50, 3627.
17. Meinwald, J.; Meinwald, Y.C.; J. Am. Chem. Soc. 1966, 88, 1305. Meinwald, J., Boriack, C.J.; Schneider, D.; Bopre, M.; Wood, W.F.; Eisner, T.; Experientia 1974, 30, 721, and refs. therein.
18. Meinwald, J.; Meinwald, Y.C.; J. Am. Chem. Soc. 1966, 88, 1305. Meinwald, J., Boriack, C.J.; Schneider, D.; Bopre, M.; Wood, W.F.; Eisner, T.; Experientia 1974, 30, 721, and refs. therein.
19. Röder, E.; Wiedenfeld, H.; Bouranel, T.; Liebigs Ann. Chem. 1985, 1708.
20. Severin, T.; Adhikary, P.; Dehmal, E.; and Eberhard, I.; Chem. Ber. 1971, 104, 2856.
21. Almstrom, K.; Ann. 1916, 411, 376.