Solid-phase synthesis of N-(buta-2,3-dien-1-yl)amides by the Crabbé reaction
Keyword(s):
The Crabbé homologation of polymer-supported propargylamine with paraformaldehyde, CuI, and dicyclohexylamine in 1,4-dioxane at 100 °C, followed by cleavage with dilute trifluoroacetic acid, furnishes N-(buta-2,3-dien-1-yl)amides as isolable products. The N-acyltriazene linker on Merrifield resin serves simultaneously as a protecting group for the nucleophilic primary amine. The product diversity is achieved by altering the acyl chloride in the acylation of the triazene linker. In addition to being a new route to nitrogen-containing allenes, our solid-phase method enables immobilization of these reactive cumulated dienes for further synthetic operations.
1998 ◽
Vol 53
(7)
◽
pp. 753-764
◽
Keyword(s):
Keyword(s):
Keyword(s):
2007 ◽
Vol 18
(4)
◽
pp. 377-379
◽
2001 ◽
Vol 42
(27)
◽
pp. 4471-4474
◽
Keyword(s):
Keyword(s):
1994 ◽
Vol 336
(3)
◽
pp. 233-236
◽
Keyword(s):
1996 ◽
Vol 227
(3)
◽
pp. 688-693
◽
Keyword(s):
2003 ◽
Vol 5
(3)
◽
pp. 273-277
◽