Formation of bicyclic β-lactams from dichloro-1,4-oxathiane-3- carboxanilides: Nucleophilic substitution of nitrogen on anomeric carbon

Heterocycles

Volumn 50, Issue 2, 1999, Pages 713-719

  Hahn, Hoh Gyu ^a   Chang, Kee Hyuk ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANILIDE; BETA LACTAM; CARBON; DICHLORO 1,4 OXATHIANE 3 CARBOXANILIDE; NITROGEN; SODIUM; SULFUR; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033117733     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-S(H)61     Document Type: Article

References (8)

1. a. T. H. Fife, R. Bembi, and R. Natarajan, J. Am. Chem. Soc., 1996, 118, 12956.
2. b. S. Winstein, L. Goodman, and R. Boschan, J. Am. Chem. Soc., 1950, 72, 2311.
3. H.-G. Hahn, K. -H. Chang, and W. S. Lee, Heterocycles, 1995, 41, 921.
4. W. S. Lee, O. S. Park, J. K. Choi, and K. D. Nam, J. Org. Chem., 1987, 52, 5374.
5. B. V. Schmeling, M. Kulka, D. S. Thiara, and W. A. Harrison, U.S. Patent 3,249,499, 1966 (Chem. Abstr., 1966, 65, 7190g).
6. 1 = 0.0428 for 979 independent reflections with I > 2σ (I) using full-matrix least-squares techniques and a structural model which incorporated anisotropic thermal parameters for all nonhydrogen atoms and isotropic thermal parameters for all hydrogen atoms.
7. Isolated yields after flash chromatography.
8. + of the corresponding phenyl isocyanate (10) was found clearly.