Synthesis of the novel thieno[4,3,2-ef][1,4]benzoxazepine ring system: 4,5-dihydro-3-(4-pyridinyl)thieno[4,3,2-ef][1,4]benzoxazepine maleate

被引:7
|
作者
Tomer, JD [1 ]
Shutske, GM [1 ]
Friedrich, D [1 ]
机构
[1] Hoechst Mar Roussel Inc, Bridgewater, NJ 08807 USA
关键词
D O I
10.1002/jhet.5570340621
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4,5-Dihydro-3-(4-pyridinyl)-thieno[4,3,2-ef][1,4]benzoxazepine maleate 2 has been synthesized from 3-amino-4-fluorobenzo[b]thiophene by employing an intramolecular nucleophilic aromatic fluoride displacement. In the presence of strong base and heat, 2 rearranges to form the isomeric hemiaminal, 3,4-dihydro-4-methyl-3-(4-pyridinyl)thieno[4,3,2-de][1,3] benzoxazine 10. A proposed mechanism for this rearrangement is discussed.
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页码:1769 / 1772
页数:4
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