A New Ring Expansion Reaction of 1-Acyl-2-vinylpiperidine and 1-Acyl-2-Vinylpiperazine via Aza-Claisen Rearrangement of Amide Enolate

1996 ◽  
Vol 26 (9) ◽  
pp. 1675-1680 ◽  
Author(s):  
Young-Ger Suh ◽  
Jee-Yeon Lee ◽  
Soon-Ai Kim ◽  
Jae-Kyong Jung
Keyword(s):  
Claisen Rearrangement ◽  
Ring Expansion ◽  
Ring Expansion Reaction

ChemInform Abstract: Ring Expansion Reaction of 2-Vinyl-4-methylene-1,3-dioxolanes to 4,5- Dihydro-3(2H)-oxepinones by Claisen Rearrangement.

ChemInform ◽  
2010 ◽  
Vol 25 (37) ◽  
pp. no-no
Author(s):  
J. SUGIYAMA ◽  
K. TANIKAWA ◽  
T. OKADA ◽  
K. NOGUCHI ◽  
M. UEDA ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Ring Expansion ◽  
Ring Expansion Reaction

Ring expansion reaction of 2-vinyl-4-methylene-1,3-dioxolanes to 4,5-dihydro-3(2H)-oxepinones by Claisen rearrangement

1994 ◽  
Vol 35 (19) ◽  
pp. 3111-3114 ◽  
Author(s):  
Jun-ichi Sugiyama ◽  
Kazuki Tanikawa ◽  
Takashi Okada ◽  
Kouichi Noguchi ◽  
Mitsuru Ueda ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Ring Expansion ◽  
Ring Expansion Reaction

Unusual Ring-Expansion Reaction of Polyfluorinated Norbornenoxetanes

Synthesis ◽  
2007 ◽  
Vol 2007 (9) ◽  
pp. 1349-1354 ◽  
Author(s):  
Viacheslav Petrov ◽  
Will Marshall
Keyword(s):  
Ring Expansion ◽  
Ring Expansion Reaction

scholarly journals An unusually rapid Claisen rearrangement involving ring expansion

2000 ◽  
pp. 2339-2340 ◽  
Author(s):  
Gianluca Dimartino ◽  
Jonathan M. Percy
Keyword(s):  
Claisen Rearrangement ◽  
Ring Expansion

Advances in Aza-Claisen-Rearrangement-Induced Ring-Expansion Strategies

2017 ◽  
Vol 6 (9) ◽  
pp. 1117-1129 ◽  
Author(s):  
Jong-Wha Jung ◽  
Seok-Ho Kim ◽  
Young-Ger Suh
Keyword(s):  
Claisen Rearrangement ◽  
Ring Expansion ◽  
Expansion Strategies

Synthesis and Ring Cyclization - Expansion - Contraction Reactions of Some New 2,2-Disubstituted Indan-1,3-diones and Related Compounds

2006 ◽  
Vol 59 (1) ◽  
pp. 59 ◽  
Author(s):  
Craig J. Roxburgh ◽  
Lee Banting
Keyword(s):  
Catalytic Hydrogenation ◽  
Pyridine Ring ◽  
Functional Group ◽  
Chemical Properties ◽  
Ring Expansion ◽  
Ring Structure ◽  
Side Reactions ◽  
The Third ◽  
Ring Expansion Reaction ◽  
Related Compounds

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.

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