In order to study the effects of N-substituents of benzomorphans on antagonist-agonist activity we synthesized several benzomorphan derivatives having N-alkenyl, alkynyl, pyranyl or oxetanylmethyl groups. Reduction of N-(hepta-2, 5-diyn-4-yl) benzomorphan (13) with Lindlar catalyst resulted in dealkylation to afford normetazocine (1), whereas reduction with diisobutylaluminum hydride gave N-(hept-2-en-5-yn-4-yl) benzomorphan (17). N-Dihydro-(14) and tetrahydropyran derivatives (15) were obtained by the reaction of 1 with 4-methoxypyrylium salt followed by reduction with sodium borohydride.
为了研究苯并
吗喃的N-取代基对拮抗剂-激动剂活性的影响,我们合成了几种具有N-烯基、炔基、
吡喃基或氧杂
环丁烷甲基基团的苯并
吗喃衍
生物。用Lindlar催化剂还原N-(庚-2,5-二炔-4-基)苯并
吗喃(13)可脱烷基化得到去甲替唑嗪(1),而用
二异丁基氢化铝还原则得到N-(庚-2-烯-5-炔-4-基)苯并
吗喃(17)。N-二氢-(14)和
四氢吡喃衍
生物(15)是通过1与
4-甲氧基吡啶鎓盐反应,然后用
硼氢化钠还原得到的。