Facile preparation of Hexahydropyrrolo
Chlorolactames 2a-f reacted with sodium azide to give the cyclopropylketimines 3a-f (75-89%), and acid hydrolysis of 3c,d yielded the cyclopropylketones 6c,d (61-67%). Compounds 3a-f and 6c, d were transformed by heating (170-240 degrees C, sublimation) to the air-sensitive dihydropyrroles 4a-f (51-71%) and dihydrofurans 7c, d (85-91%). Oxidation of the dihydro derivatives 4a-f and 7c,d with DDQ led to novel types of pyrrolo[3,2-e][1,4]diazepinedione derivatives 5a-f (75-84%) and furo[1H][3,2-e][1,4]diazepinediones 8c, d (91-93%).
Funke
C
Institut fur Organische Chemie, Georg-August-Universitat Gottingen, Tammannstrasse 2, D-37077 Gottingen, Germany, and Bayer AG, Landwirtschaftszentrum, Alfred-Nobel-Strasse 50, Geb. 6510, D-40789 Monheim, Germany.
Es-Sayed
M
de Meijere A