Dibenzo-fused seven-membered nitrogen heterocycles by a tandem reduction-lactamization reaction

被引:41
作者
Bunce, Richard A. [1 ]
Schammerhorn, James E. [1 ]
机构
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
关键词
D O I
10.1002/jhet.5570430432
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient syntheses of dibenz[b,f][1,4]oxazepin-11(10H)-one, 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and 5,11-dihydro-6H-dibenz[b,e]azepin-6-one are described using a tandem reduction-lactamization sequence. Precursors for these ring systems are available in 1-3 steps using nucleophilic aromatic substitution and Ullmann coupling methodology. Direct reduction-lactamization of these compounds using iron powder in acetic acid at 115 degrees affords the target heterocycles in >= 90% yield.
引用
收藏
页码:1031 / 1035
页数:5
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