MONONITROALKYLATIONS OF BUTANE-2,3-DIONE

Authors
PITACCO G PIZZIOLI A VALENTIN E
Citation
G. Pitacco et al., MONONITROALKYLATIONS OF BUTANE-2,3-DIONE, Synthesis, (2), 1996, pp. 242
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
2
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):2<242:MOB>2.0.ZU;2-X
Abstract
The morpholino enamine of monoprotected butane-2,3-dione reacts with c yclic and acyclic conjugated nitroalkenes in a Michael-type reaction t o yield nitro-substituted alpha-diketones, after acidic hydrolysis of the mononitroalkylated enamine adducts. Cyclopentanone, hexahydro-1H-p entalen-2-one and octahydro-2H-inden-2-one derivatives are readily obt ained by base-catalyzed intramolecular nitroaldol reaction of the acyc lic hydrolysis products.