Medium ring heterocycles: transamidation reactions of β-lactams

…, RCF Jones, S Osborne, AR Mat-Zin

Index: Crombie, Leslie; Jones, Raymond C. F.; Osborne, Steven; Mat-Zin, Ab. Rasid Journal of the Chemical Society, Chemical Communications, 1983 , # 17 p. 959 - 960

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Citation Number: 13

Abstract

Seven-, eight-, and nine-membered azalactams are easily prepared from azetidin-2-ones by transamidation via N- (halogenoalkyl) derivatives. ... The problem of constructing medium-ring saturated hetero- cycles has long exercised synthetic chemists. We have been interested in the possibility of using the strain energy of the four-membered ring, and in particular of the azetidin-2-one (p-lactam) system, as the driving force for ring expansion to medium rings. ...

~90%

~47%

~57%

~83%

~70%

~78%

~2%

β-Lactams as building blocks in the synthesis of macrocyclic...

[Wasserman, Harry H; Matsuyama, Haruo; Robinson, Ralph P Tetrahedron, 2002 , vol. 58, # 35 p. 7177 - 7190]

Reactivity of β-Lactamido N-Sulfonyl Radicals

[Begley, Michael J.; Crombie, Leslie; Haigh, David; Jones, Raymond C. F.; Osborne, Steven; Webster, Richard A. B. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993 , # 17 p. 2027 - 2046]

β-Lactams as building blocks in the synthesis of macrocyclic...

[Wasserman, Harry H; Matsuyama, Haruo; Robinson, Ralph P Tetrahedron, 2002 , vol. 58, # 35 p. 7177 - 7190]