scholarly journals Synthetic Studies on Securitinine and Related Compounds. I. Stereochemistries of the Catalytic Hydrogenation Products of 6-(4-Methoxy-2-pyridyl)-1, 4-dioxaspiro [4, 5] decan-6-ol

1972 ◽  
Vol 20 (8) ◽  
pp. 1768-1773 ◽  
Author(s):  
ZENICHI HORII ◽  
TAKESHI IMANISHI ◽  
TETSUAKI TANAKA ◽  
IKUKO MORI ◽  
MIYOJI HANAOKA ◽  
...  
ChemInform ◽  
2010 ◽  
Vol 30 (44) ◽  
pp. no-no
Author(s):  
Hideharu Suzuki ◽  
Minoru Unemoto ◽  
Mayumi Hagiwara ◽  
Takako Ohyama ◽  
Yuusaku Yokoyama ◽  
...  

2006 ◽  
Vol 59 (1) ◽  
pp. 59 ◽  
Author(s):  
Craig J. Roxburgh ◽  
Lee Banting

We have found that the hydrochloride of 2-phenyl-2-[2-(2-piperidyl)ethyl]-4,5,6,7-tetrahydroindan-1,3-dione 1 possesses marked analgesic activity (100% inhibition referenced to codeine) and report, as part of an extensive synthetic program, the synthesis of 38 new and structurally related compounds. Selective catalytic hydrogenation of the pyridine ring of 2-phenyl-2-[2-(2-pyridyl)ethyl]-indan-1,3-dione 2 yields the nine-membered nitrogen-containing heterocycle 6 by a novel ring cyclization–expansion reaction. The structural and functional group parameters required for this novel ring-expansion reaction have been extensively and thoroughly investigated through the synthesis of a series of structurally related compounds; principally by modification, substitution, and replacement of the various functionality contained within 2. In addition, we report the synthesis of a series of new 2-methyl-2-(ω-N-phthalimidoalkyl)-indan-1,3-diones 41, 45, and 53, two of which, like the parent 2-phenyl substituted indan-1,3-dione 2, also undergo a novel ring cyclization–expansion reaction to yield eight- and nine-membered nitrogen-containing rings. However, in these cases, further transannular reactions occur to produce the new 5,5- and 5,6-ring-fused nitrogen-containing heterocycles 44, 48 and 51, 52. Hydrazinolysis of the third, 2-methyl-2-(4-N-phthalimidobutyl)-indan-1,3-dione yields the new azepine-containing ring structure 56 by direct cyclization. Furthermore, some interesting and unexpected chemical properties of the final compounds, which include selective and non-selective pyridine-ring hydrogenations and a few unexpected side reactions, are described.


1996 ◽  
Vol 44 (1) ◽  
pp. 55-61 ◽  
Author(s):  
Masanobu TANI ◽  
Takahiro ARIYASU ◽  
Masanori OHTSUKA ◽  
Terumi KOGA ◽  
Yumi OGAWA ◽  
...  

1997 ◽  
Vol 45 (11) ◽  
pp. 1739-1744 ◽  
Author(s):  
Yasuoki MURAKAMI ◽  
Toshiko WATANABE ◽  
Hideharu SUZUKI ◽  
Nobuyo KOTAKE ◽  
Tomoko TAKAHASHI ◽  
...  

Tetrahedron ◽  
1994 ◽  
Vol 50 (21) ◽  
pp. 6239-6258 ◽  
Author(s):  
Tadashi Katoh ◽  
Masayuki Kirihara ◽  
Yuriko Nagata ◽  
Yuko Kobayashi ◽  
Katsuko Arai ◽  
...  

Heterocycles ◽  
2002 ◽  
Vol 56 (1-2) ◽  
pp. 519 ◽  
Author(s):  
Yasuoki Murakami ◽  
Hideharu Suzuki ◽  
Tomoko Furukawa ◽  
Chiaki Yamada ◽  
Ichiro Shibuya ◽  
...  

Heterocycles ◽  
1979 ◽  
Vol 13 (1) ◽  
pp. 411 ◽  
Author(s):  
Tetsuji Kametani ◽  
Kimio Takahashi

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