Subscribe to RSS
DOI: 10.1055/s-2002-33652
A High-Yielding General Synthesis of α-Lactams [1]
Publication History
Publication Date:
05 September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200212/lookinside/thumbnails/10.1055-s-2002-33652-1.jpg)
Abstract
A high-yielding general synthesis of α-lactams (aziridinones) is described. An α-haloamide 1 precursor is cyclized by sodium hydride in the presence of 15-crown-5 ether at room temperature, using dichloromethane as the solvent. The by-products, hydrogen gas and sodium halide, are easily removed. The yields for the six known α-lactams (2b-g) chosen for this study are comparable or superior to previously reported yields, [6] [7] [11] [19-21] yet only short reaction times and a simple work-up is required.
Key words
aziridinones - dehydrohalogenation - heterocycles - ring closure
Part of this work was presented at the 223rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002, Division of Organic Chemistry, Abstract 350.
- 2
Hoffman RV. In The Amide Linkage: Selected Structural Aspects in Chemistry Biochemistry and Material ScienceGreenberg A.Breneman CM.Liebman JF. John Wiley & Sons Inc.; New York: 2000. p.137-155 - 3
Lengyel I.Cesare V.Chen S.Taldone T. Heterocycles 2002, 57: 677 - 4
Tantillo JD.Houk KN.Hoffman RV.Tao J. J. Org. Chem. 1999, 64: 3830 - 5
Talaty ER.Yusoff MM. Chem. Commun. 1998, 985 - 6
Sheehan JC.Lengyel I. J. Am. Chem. Soc. 1964, 86: 1356 - 7
Lengyel I.Cesare V.Karram H.Taldone T. J. Heterocycl. Chem. 2001, 38: 997 - 8
Lengyel I.Sheehan JC. Angew. Chem., Int. Ed. Engl. 1968, 7: 25 ; Angew. Chem. 1968, 80, 27 - 9
Quast H.Meichsner G.Seiferling B. Chem. Ber. 1987, 120: 217 - 10
Scrimin P.D’Angeli F.Veronese AC. Synthesis 1982, 586 - 11
Lengyel I.Cesare V.Taldone T.Uliss D. Synth. Commun. 2001, 31: 3671 - 13
Backes J. In Houben-Weyl Methoden der Organischen Chemie Vierte Auflage Band E16b, Georg Thieme Verlag; Stuttgart: 1991. p.1 - 14
Bladon CM.Kirby GW. J. Chem. Soc., Chem. Commun. 1982, 1402 -
15a
Hoffman RV.Nayyar NK. J. Org. Chem. 1995, 60: 7043 -
15b
Hoffman RV.Nayyar NK. J. Org. Chem. 1995, 60: 5992 -
15c
Hoffman RV.Nayyar NK. J. Org. Chem. 1993, 58: 2355 -
15d
Hoffman RV.Nayyar NK.Kline Kole BW. J. Am. Chem. Soc. 1992, 114: 6262 -
15e
Hoffman RV.Nayyar NK.Chen W. J. Org. Chem. 1992, 57: 5700 -
16a
Sarel S.Greenberger A. J. Org. Chem. 1958, 23: 330 -
16b
Sarel S.Leader H. J. Am. Chem. Soc. 1960, 82: 4752 -
16c
Sarel S.Klug JT. Isr. J. Chem. 1964, 2: 143 -
16d
Sarel S.D’Angeli F.Klug JT.Taube A. Isr. J. Chem. 1964, 2: 167 -
16e
Sarel S.Klug JT.Breuer E.D’Angeli F. Tetrahedron Lett. 1964, 1553 -
17a
Sheehan JC.Frankenfeld JW. J. Am. Chem. Soc. 1961, 83: 4792 -
17b
Sheehan JC.Beeson JH. J. Org. Chem. 1966, 31: 1637 - 18
Aspinall HC.Greeves N.Lee W.McIver EG.Smith PM. Tetrahedron Lett. 1997, 38: 4679 - 19
Lengyel I.Uliss DB. J. Chem. Soc., Chem. Commun. 1968, 1621 - 20
Sheehan JC.Beeson JH. J. Am. Chem. Soc. 1967, 89: 362 - 21
Bott K. Angew. Chem., Int. Ed. Engl. 1967, 6: 946 - 22
Lengyel I.Aaronson MJ. Can. J. Spectroscopy 1974, 19: 95
References
Part of this work was presented at the 223rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002, Division of Organic Chemistry, Abstract 350.
12Unpublished results from the authors’ laboratory.