SYNTHESIS OF ISOQUINOLINE DERIVATIVES BY A TANDEM AZA-WITTIG ELECTROCYCLIZATION STRATEGY AND PREPARATION OF THE UNKNOWN 1,9-DIAZAPHENALENE RING BY A CONSECUTIVE ELECTROCYCLIC RING-CLOSURE CLAISEN REARRANGEMENT INTRAMOLECULAR AMINATION PROCESS

被引:43
作者
MOLINA, P
ALAJARIN, M
VIDAL, A
机构
[1] Departamento de Quimica Orgánica, Facultad de Ciencias, Universidad de Murcia, Campus de Espinardo
关键词
D O I
10.1021/jo00312a020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of iminophosphorane 3, derived from ethyl a-azido-2-(allyloxy)cinnamate, with aromatic isocyanates in toluene at 150 °C leads to the corresponding isoquinoline derivatives 5 by a tandem electrocyclic ring closure/Claisen rearrangement of the intermediate carbodiimide. Fremy's salt promoted oxidation of compounds 5 yields the 5,8-isoquinolinequinone allides 6, which by heating undergo cyclization to 2H-pyrano[2,3-f]isoquinolines 7. Iminophosphorane 14, derived from ethyl a-azido-2-(allyloxy)-3-methoxycinnamate, reacts with aromatic isocyanates to give the corresponding carbodiimides, which by thermal treatment at 150 °C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/intramolecular amination process to give 1,9-diazaphenalene derivatives 18 in moderate yields. © 1990, American Chemical Society. All rights reserved.
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页码:6140 / 6147
页数:8
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