A Synthetic Route to the Morphan Ring System by Skeletal Transformation of Norbornadiene
作者:Hiroo Inoue、Toshiki Origuchi、Katsumi Umano
DOI:10.1246/bcsj.57.806
日期:1984.3
The morphan skeleton was prepared from 2-phenylsulfonyl-2-azabicyclo[3.2.1]oct-6-ene (2), derived from norbornadiene, through the addition of dichlorocarbene to the monoene 2 and the subsequent thermal isomerization of the adduct obtained. The isomerization products, 2-phenylsulfonyl-6,7-dichloro-2-azabicyclo[3.3.1]non-7-ene and 2-phenylsulfonyl-7,8-dichloro-2-azabicyclo[3.3.1]non-6-ene, which are
吗喃骨架是由 2-苯基磺酰基-2-氮杂双环 [3.2.1] oct-6-烯 (2) 制备的,该物质源自降冰片二烯,通过将二氯卡宾加成到单烯 2 中并随后对所得加合物进行热异构化。异构化产物2-苯基磺酰基-6,7-二氯-2-氮杂双环[3.3.1]non-7-ene和2-苯基磺酰基-7,8-二氯-2-氮杂双环[3.3.1]non-6-烯在氯化锂存在下可相互转化,通过还原脱氯和烷基化作用转化为各种吗喃。此外,通过 1,2,4,5-四嗪-3,6-二甲酸二甲酯与 2-苯基磺酰基-2-氮杂双环[3.3.1]non-6-的环加成反应合成了 6,7-哒嗪基-退火吗喃。烯。