Facile Syntheses of Azetidin-3-ols by Rearrangement of 2,3-Epoxypropylamines

Synthetic Communications

Volumn 33, Issue 24, 2003, Pages 4297-4302

  Oh, Chang Ho ^a   Rhim, Chul Yun ^a   You, Choong Ho ^a   Cho, Jin Rai ^b  

^a Hanyang University   (South Korea)

^b Agency for Defence Development   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 EPOXYPROPYLAMINE DERIVATIVE; ACETONITRILE; AZETIDIN 3 OL DERIVATIVE; AZETIDINE DERIVATIVE; PROPYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0346433971     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026859     Document Type: Article

References (12)

1. (a) Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P.R. Synthesis of 1,3,3-trinitroazetidine via the oxidative nitrolysis of N-p-tosyl-3-azetidinone oxime. J. Org. Chem. 1995, 60, 1959;
2. (b) Anthoni, U.; Christensen, D.H.; Christophersen, C.; Gajhede, M.; Henriksen, G.; Nielsen, O.; Nielsen, P.H. Hydrogen bonding in 3-azetidinol. Journal of Molecular Structure 1990, 220, 43.
3. (a) Achibald, T.G.; Giraldi, R.; Baum, K.; George, C. Synthesis and X-ray crystal structure of 1,3,3-trinitroazetidine. J. Org. Chem. 1990, 55, 2920;
4. (b) Katrizky, A.R.; Cundy, D.J.; Chen, J. Novel syntheses of 1,3,3-trinitroazetidine. J. Heterocyclic Chem. 1994, 31, 271.
5. (a) Gaertner, V.R. Cyclization of 1-alkylamino-3-halo-2-alkanols to 1-alkyl-3-azetidinols. Tetrahedron Lett. 1966, 4691;
6. (b) Gaertner, V.R. Cyclization of 1-alkylamino-3-halo-2-alkanols to 1-alkyl-3-azetidinols. J. Org. Chem. 1967, 2972.
7. Okutani, T.; Kaneko, T.; Masuda, K. Azetidine derivatives. I. Synthesis 3-substituted azetidine derivatives. Chem. Pharm. Bull. 1974, 22, 1490.
8. Gaj, B.J.; Moore, D.R. Substituted 1-alkyl-3-azetidinols. Tetrahedron Lett. 1967, 2155.
9. (a) Jenkins, H.; Cale, A.D. German Offen. 1970, 1,932,219; 1-Alkyl-3-azetidinole und verfahren zu deren herstellung. Chem Abstr. 1970, 72, 100478s;
10. (b) Higgins, R.H.; Eaton, Q.L.; Worth, L., Jr.; Peterson, M.V. Preparation of 3-azetidinols with non-bulky 1-alkyl substituents. J. Heterocyclic Chem. 1987, 24, 255;
11. (c) Higgins, R.H.; Watson, M.R.; Faircloth, W.J. Preparations of trimethylsilyl ethers of 3-azetidinols. Scope and limitations. J. Heterocyclic Chem. 1988, 25, 383.
12. Karikomi, M.; Arai, K.; Toda, T. Steroselective synthesis of 3-hydroxyazetidines via regioselective hydrogenation of 2,3-epoxyamines by using magnesium bromide. Tetrahedron Lett. 1997, 38, 6059.