75377-01-4Relevant academic research and scientific papers
Base-catalyzed intramolecular Diels-Alder cyclization of dialkyl(3-arylprop-2-yn-1-yl)-(3-phenylprop-2-en-1-yl)ammonium bromides in aqueous solution
Chukhajian,Ayrapetyan,Chukhajian, El. O.,Panosyan
, p. 1274 - 1280 (2014/01/17)
Dialkyl(3-arylprop-2-yn-1-yl)(3-phenylprop-2-en-1-yl)ammonium bromides, in contrast to their allyl analogs containing a 3-arylprop-2-en-1-yl group, undergo cyclization in aqueous solution in the presence of base upon prior heating to give potentially biologically active 2,2-dialkyl-6-chloro-4-phenyl-3a,4- dihydrobenzo[f]isoindolinium bromides in almost quantitative yield. Heat is released in the course of these reactions. We found that the introduction of a phenyl group at position 3 of the allyl fragment facilitates the cyclization. This is the first report of a base-catalyzed intramolecular cyclization of allyl analogs of dialkyl(3-arylprop-2-yn-1-yl)ammonium salts.
Cyclization of dialkyl(3-phenylpropen-2-yl)-(3-phenylpropyn-2-l)ammonium bromides by the action of an aqueous alkali solution. aqueous-alkaline cleavage of the cyclization products - N,n-dialkyl-4(9)-phenyl-3a,4-dihydro-benzo[f] isoindolinium bromides
Chukhajian,Ayrapetyan,Chukhajian, El. O.,Panosyan
, p. 1314 - 1320 (2013/04/24)
When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3- phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N-dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)-N(2) or N(2)-C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)-N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9- phenyl-3a,4-dihydrobenzo-[f]isoindolinium bromide.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 6. The Rearrangements of Diallyl- and Allylpropynyl-ammonium Cations in Protic Media
Laird, Trevor,Ollis, W. David,Sutherland, Ian O.
, p. 1477 - 1486 (2007/10/02)
The base catalysed rearrangements of the cations (1d-j) in aqueous solution yield the isomeric cations (15) or the aldehydes (10) and (11), or mixtures of (15), (10), and (11).This contrasts dramatically with the transformations observed for the cations (1) in aprotic solvents.The cations (15) undergo Hofmann elimination to the naphthalenic amines (12) or (13) and (14).The methiodide of amine (13g) shows a novel consequence of restricted rotation.The n.m.r. spectrum of the methiodide shows that the two protons of the methylene group are diastereotopic.
