1071836-41-3Relevant academic research and scientific papers
Synthesis of functionalized isobenzomorphans by two-step cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with isoquinolines
Yawer, Mirza A.,Hussain, Ibrar,Guetlein, Joerg-Peter,Schmidt, Andreas,Jiao, Haijun,Reinke, Helmut,Spannenberg, Anke,Fischer, Christine,Langer, Peter
, p. 4193 - 4199 (2008)
A great variety of functionalized 7,8-benzo-anellated 9-azabicyclo-[3.3.1] nonan-3-ones were prepared by methyl or benzyl chloroformate-mediated condensation of isoquinolines with 1,3-bis(silyloxy)-1,3-butadienes and subsequent TFA-mediated cyclization. The hydroxy group could be functionalized by Suzuki reactions of the corresponding enol triflates. The N-benzyloxycarbonyl-substituted products were successfully deprotected. The decarboxylation allowed the synthesis of the parent 7,8-benzo-anellated 9-azabicyclo[3.3.1]nonan-3-ones. The products can be regarded as functionalized isobenzomorphans - simple structural analogues of morphine. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
