Direct Alkylation of 2-Acylamino- and 2-Aminopyrazines with Organolithium Reagents

Synlett

Volumn 1996, Issue 10, 1996, Pages 1015-1017

  Nakamura, Hideshi ^a   Aizawa, Mihoko ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542733709     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5651     Document Type: Article

References (12)

1. Shimomura, O.; Musicki, B.; Kishi, Y. Biochem. J. 1988, 251, 405-410: 1989, 261, 913-920: and references are cited therein. Goto, T. In Marine Natural Products, Vol. 3; P. J. Scheuer Ed.; Academic Press: New York, 1984; p 179-221
2. Shimomura, O.; Musicki, B.; Kishi, Y. Biochem. J. 1988, 251, 405-410: 1989, 261, 913-920: and references are cited therein. Goto, T. In Marine Natural Products, Vol. 3; P. J. Scheuer Ed.; Academic Press: New York, 1984; p 179-221
3. Shimomura, O.; Musicki, B.; Kishi, Y. Biochem. J. 1988, 251, 405-410: 1989, 261, 913-920: and references are cited therein. Goto, T. In Marine Natural Products, Vol. 3; P. J. Scheuer Ed.; Academic Press: New York, 1984; p 179-221
4. A. K. Campbell. Chemiluminescence: Principle and Applications in Biology and Medicine; Ellis Horwood Ltd.: Chichester, England, 1988. Shimomura, O. Biochem. J. 1995, 306, 537-543. Ohmiya, Y.; Hirano, T. Chemistry & Biology, 1996, 3, 337-347.
5. A. K. Campbell. Chemiluminescence: Principle and Applications in Biology and Medicine; Ellis Horwood Ltd.: Chichester, England, 1988. Shimomura, O. Biochem. J. 1995, 306, 537-543. Ohmiya, Y.; Hirano, T. Chemistry & Biology, 1996, 3, 337-347.
6. A. K. Campbell. Chemiluminescence: Principle and Applications in Biology and Medicine; Ellis Horwood Ltd.: Chichester, England, 1988. Shimomura, O. Biochem. J. 1995, 306, 537-543. Ohmiya, Y.; Hirano, T. Chemistry & Biology, 1996, 3, 337-347.
7. Nakamura, H.; Takeuchi, D.; Murai, A. Synlett, 1995, 1277-1278.
8. Snieckus, V. Chem. Rev. 1990, 90, 879-933.
9. Turck, A.; Plé , N.; Trohay, D.; Ndzi, B.; Quéguiner, G., J. Heterocyclic Chem. 1992, 29, 699-702.
10. The alkylation product of 2-pivaloylaminopyrazine with t-butyllithium followed by quenching with benzaldehyde was reported to be 3-benzyl-5-t-butyl-2-pivaloylaminopyrazine on the basis of the coupling constant between pyrazine proton and benzyl methylene proton in lit. 5. They also reported that orthometalation of 2-pivaloylaminopyrazine was achieved with lithium 2,2,6,6-tetramethylpiperizine in 25% yield.
11. Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J. P. Tetrahedron Lett. 1982, 23, 5291-5294.
12. Alkylation of pyrazine with an oraganolithium reagent was first repoted by Klein, B.; Spoerri, P. E. J. Am. Chem. Soc. 1950, 72, 1844. They reported that hydrogen gas was evolved when the reaction was quenched with water.