Search for a nonelectrocyclic cyclization of nitrosostyrene: Rearrangements of Michael adducts from DMAD and alpha-dialkylamino oximes

Coskun N., Arikan N.

TURKISH JOURNAL OF CHEMISTRY, cilt.27, sa.1, ss.15-20, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 1
  • Basım Tarihi: 2003
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.15-20
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

The aza-Claisen rearrangement product of the Michael adducts 2 from alpha-dialkylaminoacetophenone oximes and DMAD underwent fragmentation to give dialkylaminomaleate, and benzonitrile at reflux in acetonitrile. The fragmentation was assumed to proceed through an unstable 4H-1,2-oxazete 6. The same reaction performed at room temperature, in addition to the nitrile and maleate, gave the corresponding 2-(2-dialkylamino-1-phenylethylideneaminooxy)-but-2-enedioic acid dimethyl esters 8 and 9. Compounds 9 isomerized to 8 on heating in acetonitrile.