Dibenzo[a,d]cycloheptene and Related Compounds. III. The Synthesis of Some Analogues of Methadone Containing the Dihydrodibenzo[a,d]cycloheptene and the Tetrahydrodibenzo[a,d]cyclooctene Ring Systems

1971 ◽  
Vol 49 (3) ◽  
pp. 485-492 ◽  
Author(s):  
D. E. Horning ◽  
J. M. Muchowski

The synthesis and spectral properties of some two- and three-carbon ortho-bridged analogues of the analgesic methadone are described. These compounds were devoid of analgesic activity.

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3356-3368
Author(s):  
Piotr Pomarański ◽  
Zbigniew Czarnocki

The synthesis of novel l-prolinal dithioacetal and its application as an organocatalyst for the direct Michael addition of cyclic ketones and acetophenone derivatives to trans-β-nitrostyrene and related compounds is described. The prolinal dithioacetal acts as effective catalyst in the case of cyclic ketones of different ring size, in particular five- and six-membered examples, as well as larger and smaller ring systems. High enantioselectivity and diastereoselectivity is observed for different substrates and trans-β-nitrostyrenes. Also, the first asymmetric syntheses of selected 2-methyl-4-nitro-1,3-diphenylbutan-1-one derivatives by application of the obtained organocatalyst is presented.


2015 ◽  
Vol 96 (6) ◽  
pp. 1974-1981 ◽  
Author(s):  
Anne Linn Hykkerud Steindal ◽  
Tor J Johansen ◽  
Gunnar B Bengtsson ◽  
Sidsel F Hagen ◽  
Jørgen AB Mølmann

2006 ◽  
Vol 82 (6) ◽  
pp. 1645-1650 ◽  
Author(s):  
Zhu Fengqiang ◽  
Jiro Motoyoshiya ◽  
Junji Nakamura ◽  
Yoshinori Nishii ◽  
Hiromu Aoyama

1960 ◽  
Vol 38 (11) ◽  
pp. 2152-2160 ◽  
Author(s):  
R. A. Abramovitch ◽  
K. A. H. Adams ◽  
A. D. Notation

The first unambiguous synthesis of δ-carboline has been achieved starting with 3-amino-2-phenylpyridine. This was converted to the azide which was thermally cyclized to δ-carboline. The carboline gave a py-N-methiodide which was converted to the anhydronium base. The pKa of the anhydronium base was determined and its significance is discussed. The anhydronium base formed a methiodide which, on dry distillation, gave ind-N-methyl-δ-carboline. The spectral properties of the various derivatives of δ-carboline were examined and the bond structures of the anhydronium base and the methiodides are discussed.


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