From furans to anilines: toward one-pot two-step amination/diels-alder sequences.
Raouf Medimagh, Sylvain Marque, Damien Prim, Saber Chatti, Hédi Zarrouk
Index: J. Org. Chem. 73(6) , 2191-7, (2008)
Full Text: HTML
Abstract
Selective metal-free amination and Diels-Alder reactions are described in the furan series, leading to polysubstituted anilines or to stable oxabicyclic adducts in high yield. Interestingly, anilines are conveniently prepared through a novel one-pot, two-step amination/Diels-Alder procedure from commercially available 5-bromo-2-furaldehyde.
Related Compounds
Related Articles:
5-Substituted-2-furaldehydes: a synthetic protocol utilizing an organozinc route.
2013-03-01
[J. Org. Chem. 78(5) , 1984-93, (2013)]
Efficient coupling of heteroaryl bromides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst. Feuerstein M, et al.
[Tetrahedron Lett. 42(23) , 5659-62, (2001)]
Efficient and Simple Synthesis of 6-Aryl-1,4-dimethyl-9H-carbazoles. Caruso A, et al.
[Molecules 13(6) , 1312-1320, (2008)]
A synthesis strategy yielding skeletally diverse small molecules combinatorially. Burke MD, et al.
[J. Am. Chem. Soc. 126(43) , 14095-14104, (2004)]
Furan derivatives. LXXXV11. The synthesis and ultraviolet spectra of 5-(4-X-phenyIsulfonyI)-2-furaldehydes and 2-cyano-3-[5-(4-X-phenyl-sulfonyl)-2-furyl] acrylonitriles. Kada R and Kovác J.
[Chemical Papers (Slovak Acad. Sci.) 30(4) , 502-507, (1976)]