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Stereoselective Michael addition of 6‐amino‐1,3‐dimethyl‐2,4‐pyrimidinedione to the exocyclic methylene of three sesquiterpene lactones. 1 H and 13 C NMR evidence of a new C‐C bond and lactam formation
Author(s) -
Dfaz Eduardo,
Barrios Hector,
Nava Jose Luis,
Enriquez Raul G.,
Guzmán Angel,
Leticia León G.,
Fuentes Jose Fernando,
Aidee Fuentes B.,
Quintero Angelina,
Solano Jose Dolores
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340351
Subject(s) - chemistry , stereoselectivity , methylene , lactone , ring (chemistry) , stereochemistry , sesquiterpene , lactam , pyrimidine , derivative (finance) , michael reaction , double bond , sesquiterpene lactone , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
The Stereoselective addition of the pyrimidine derivative 1 to the exocyclic methylene of the α,β unsaturated dehydrocostus lactone 2, Ivalin acetate 3 and Zaluzanin A diacetate 4, was achieved resulting in a new C‐C bond formation. In the cases of compounds 3 and 4, after the addition, the lactone was cleaved followed by reclosure into a lactam ring system.