72349-31-6Relevant academic research and scientific papers
Concise Synthesis of 4-Arylquinolines via Intramolecular Cyclization of Allylamines and Ketones
Wei, Wen-Tao,Cheng, Ya-Juan,Hu, Yu,Chen, Yan-Yan,Zhang, Xue-Jing,Zou, Yong,Yan, Ming
supporting information, p. 3474 - 3478 (2016/01/25)
The intramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert-butoxide and N,N-dimethylformamide. A series of 4-arylquinolines was prepared in good yields. The reaction could be accomplished at room temperature using only a substoichiometric amount of potassium tert-butoxide. On the other hand, the reaction of the structurally analogous allyl ethers afforded diverse products. The reaction may proceed via the rearrangement of α-aminoallyl radicals and the generation of nucleophilic enamine intermediates. This finding represents a new strategy for the synthesis of quinoline derivatives from readily available 2-(allylamino)phenyl ketones.
Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones
Susanti, Dewi,Ng, Linda Li Ru,Chan, Philip Wai Hong
supporting information, p. 353 - 358 (2014/05/20)
2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)- mediated 1,2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel in n-hexane/ ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.
Gas-phase Rearrangement and Cyclisation Reactions of 2-Benzylphenylaminyl Radicals and Related 2-Hetero-analogues
Cadogan, J. I. G.,Hickson, Clare L.,Hutchison, H. Susan,McNab, Hamish
, p. 377 - 384 (2007/10/02)
Gas-phase pyrolysis of the appropriate N-allyl or N-benzyl compound leads to the aminyl radicals 1 (X = NH, Y = CH2, CO, S, or O).Equilibration of these via the spirodienyl 2 gives mixtures of isomeric acridans or acridones as major products from radicals 1 (X = NH, Y = CH2 and Y = CO, respectively) and isomeric phenothiazines as minor products from radical 1 (X = NH, Y = S).The major product in this case is the aminodibenzofuran 29 which may be formed by H-abstraction by the aminyl to give an aryl radical, followed by cyclisation (Scheme 6).The only cyclised product from radical 1 (X = NH, Y = O) is the carbazole 35, formed by a mechanism similar to that of Scheme 6, but in which H-abstraction by the rearranged phenoxyl radical has taken place.
