6283-41-6Relevant academic research and scientific papers
A Short synthesis of benzomorphane analgesics (±)-Metazocine and (±)-Phenazocine
Singh, Kamal Nain,Singh, Pushpinder,Sharma, Arvind Kumar,Singh, Paramjit,Kessar, Satinder V.
experimental part, p. 3716 - 3720 (2010/12/29)
A three step synthesis of (±)-metazocine and (±)-phenazocine starting with 3,4-lutidine is described. The key step involves Lewis acid promoted lithiation/electrophilic substitution reaction of N-alkyl-3,4-dimethyl- 1,2,5,6- tetrahydropyridine. Copyright
[2+ + 4] Cycloadditions of iminium ions - Concerted or stepwise mechanism aza Diels - Alder reactions?
Mayr, Herbert,Ofial, Armin R.,Sauer, Juergen,Schmied, Bernhard
, p. 2013 - 2020 (2007/10/03)
The N,N-dimethylmethyleneammoninm ion 1 reacts regio- and stereoselectively with the 1,3-dienes 2a-2f to yield the 1,2',5,6- tetrahydropyridinium ions 3. The kinetics of these hetero Diels-Alder reactions, which have been followed by dilatometry and
Benzomorphans useful as NMDA receptor antagonists
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, (2008/06/13)
Compounds of the formula I STR1 are disclosed. In this formula, R is a member selected from the group consisting of --CR 1 R 2 R 3, hydroxy, an alkoxy group having 1 to 4 carbon atoms and --NR 4 R 5, in which at most one of R 1, R 2 and R 3 is hydrogen and the remainder are each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkylalkyl having 4 to 9 carbon atoms and a 3 to 6 membered cyclic ether; R 4 and R 5 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms; R 6 and R 7 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms; and R 8 is hydrogen, an alkyl group having 1 to 4 carbon atoms, hydroxy, an alkoxy group having 1 to 4 carbon atoms or halogen. Salts of these compounds are also disclosed. Also disclosed are pharmaceutical compositions of these compounds with a pharmaceutically acceptable carrier, the use of these materials as N-methyl-D-aspartate receptor antagonists, processes for preparing these compounds and salts, and methods to treat cerebral diseases by administering an effective amount of these compounds, salts or compositions.
GEAR EFFECT-10 CONFORMATIONAL ASPECTS OF THE POSITIVE OR NEGATIVE BUTTRESSING EFFECTS OF METHYL GROUPS: POLYMETHYLPYRIDINES
Roussel, Christian,Balaban, Alexandru T.,Berg, Ulf,Chanon, Michel,Gallo, Roger,et al.
, p. 4209 - 4220 (2007/10/02)
The effects of the shape of a methyl group on reactivity, which cannot be accounted for by considering a methyl group as a spherical subtituent with the appropriate van der Waals radius, was considered in kinetics of alkylation of substituted pyridines and barriers to rotation and ground state conformations of an isopropyl group attached to a planar framework.The perturbation of a methyl group by an o-methyl group is accounted for by a unique conformational explanation which involves the polyhedral shape of the methyl group.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 7. The Rearrangements of Allyl(pentadienyl)- and Propionyl(pentadienyl)-ammonium Cations. The Sigmatropic Rearrangement.
Laird, Trevor,Ollis, W. David,Sutherland, Ian O.
, p. 2033 - 2048 (2007/10/02)
The base catalysed rearrangements of the cations (7), (17), (22), and (27) gave the enamines (9), (18), (23), and (28), which on hydrolysis yielded the aldehyde (10), (19), (24), and (29) respectively.The reactions are shown to be concerted sigmatropic rearrangements proceeding via a nine-membered transition state involving 10? electrons.The base catalysed rearrangements of the 3-phenylprop-2-ynyl (pentadienyl) ammonium cations (51), (52), (60), and (61), however yield only the products of , , and sigmatropic rearrangements.
