Efficient synthesis of primary selenocarboxylic amides by reaction of nitriles with phosphorous(V) selenide

Synlett

Volumn , Issue 12, 2002, Pages 1983-1986

  Geisler, Karlheinz ^a   Jacobs, Anke ^a   Künzler, Andreas ^a   Mathes, Manuela ^a   Girrleit, Ilona ^a   Zimmermann, Birgit ^a   Bulka, Ehrenfried ^a   Pfeiffer, Wolf Diethard ^a   Langer, Peter ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Cyclizations; Heterocycles; Nitriles; Selenium; Synthetic methodology

Indexed keywords

ALCOHOL; AMIDE; CARBOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; NITRILE; PHOSPHORUS DERIVATIVE; SELENIDE; SELENIUM DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; METHODOLOGY; SYNTHESIS;

EID: 0036458153     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35604     Document Type: Article

References (19)

1. Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein.
2. (a) Larsen, R. In Comprehensive Heterocyclic Chemistry II, Vol. 3; Shinkai, I., Ed.; Elsevier Science: Oxford, 1996, Chap. 8.
3. (b) Wirth, T. Organoselenium Chemistry, Modern Developments in Organic Synthesis; Springer: Berlin, 2000.
4. (c) Koketsu, M.; Nada, F.; Ishihara, H. Synthesis 2002, 195; and references cited therein.
5. (a) Lai, L.-L.; Reid, D. H. Synthesis 1993, 870.
6. (b) Klayman, D. L.; Griffins, T. S. J. Am. Chem. Soc. 1973, 95, 197.
7. 4/Se, see: Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408.
8. (d) Also see: Koketsu, M.; Fukuta, Y.; Ishihara, H. Tetrahedron Lett. 2001, 42, 6333.
9. Ogawa, A.; Miyaka, J.; Karasaki, Y.; Murai, S.; Sonoda, N. J. Org. Chem. 1985, 50, 384.
10. Kaminski, R.; Glass, R. S.; Skowronska, A. Synthesis 2001, 1308.
11. Cohen, V. J. Synthesis 1978, 668.
12. 3 is very prone to hydrolysis and has to be handled with great care (glove box). Since it has to be used as a powder, substantial decomposition readily occurs and impurities cannot be separated.
13. 3 is very prone to hydrolysis and has to be handled with great care (glove box). Since it has to be used as a powder, substantial decomposition readily occurs and impurities cannot be separated.
14. For the synthesis of thioamides from amides, see: Raucher, S.; Klein, P. J. Org. Chem. 1981, 46, 3558.
15. For the synthesis of N,N-disubstituted selenocarboxylic amides, see: (a) Collhard-Charon, C.; Renson, M. Bull. Soc. Chim. Belg. 1963, 72, 304. (b) Jensen, K. A.; Nielsen, P. H. Acta Chim. Scand. 1966, 20, 597. (c) See also: Sukhai, R. S.: de Jong, R.; Brandsma, L. Synthesis 1977, 888.
16. For the synthesis of N,N-disubstituted selenocarboxylic amides, see: (a) Collhard-Charon, C.; Renson, M. Bull. Soc. Chim. Belg. 1963, 72, 304. (b) Jensen, K. A.; Nielsen, P. H. Acta Chim. Scand. 1966, 20, 597. (c) See also: Sukhai, R. S.: de Jong, R.; Brandsma, L. Synthesis 1977, 888.
17. For the synthesis of N,N-disubstituted selenocarboxylic amides, see: (a) Collhard-Charon, C.; Renson, M. Bull. Soc. Chim. Belg. 1963, 72, 304. (b) Jensen, K. A.; Nielsen, P. H. Acta Chim. Scand. 1966, 20, 597. (c) See also: Sukhai, R. S.: de Jong, R.; Brandsma, L. Synthesis 1977, 888.
18. 5 as a grey solid. For comparison, see: Kudchadker, M. V.; Zingaro, R. A.; Irgolic, K. J. Can. J. Chem. 1968, 46, 1415.
19. 11NSe (284.22): C 63.39, H 3.90, N 4.93; found C 63.45, H 3.92, N 4.91. All new compounds gave satisfactory analytical or high resolution mass data.