15332-67-9Relevant academic research and scientific papers
Effective monoallylation of anilines catalyzed by supported KF
Pace, Vittorio,Martinez, Fernando,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
, p. 2661 - 2664 (2008/02/08)
Equation Presented A mild and straightforward monoallylation procedure for different anilines is described using the efficient, inexpensive, noncorrosive, and environmentally friendly reagent KF-Celite. By using only a 1/1.2 stoichiometric ratio of electrophilic reagent to aniline, in very short reaction times, the monoallylated products are obtained in high isolated yields via this procedure, which works very effectively regardless of the electronic nature of the substituent on the ring, although electron withdrawing groups make the reactions go even faster.
Direct palladium/carboxylic acid-catalyzed allylation of anilines with allylic alcohols in water
Yang, Shyh-Chyun,Hsu, Yi-Chun,Gan, Kim-Hong
, p. 3949 - 3958 (2007/10/03)
The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of anilines using allylic alcohols directly gave allylic anilines in good yields.
Iron-catalyzed transformations of 2-chloro-1,6-heptadienes
Necas, David,Kotora, Martin,Cisarova, Ivana
, p. 1280 - 1285 (2007/10/03)
(Phosphane)iron complexes in the presence of excess trialkylaluminium reagents catalyze various transformations of 2-chloro-α,ω-dienes, depending on their structure. Most notably, in the cases of simple 2-chloro-1,6-heptadienes, cyclization with transfer of the alkyl group (Me and Et) from the corresponding trialkylaluminium compound was observed to give 2-alkyl-1-methylidenecyclopentanes. Reaction with 2-chloro-1,7-octadiene afforded the product of reductive dehalogenation. In the case of 2-chloro-4-aza-1,6-heptadiene a partial or complete hydrogenation of the double bonds was observed depending on the amount of trialkylaluminum reagent used. Interestingly, allyl(2-chloroallyl)malonate underwent C-C bond cleavage with the loss of an allyl group to give (2-chloroallyl)malonate. In the presence of ruthenium catalysts only reductive dehalogenation was observed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
N-Chloroallylation of Aniline with 1,2,3-Trichloropropane
Nazarov,Magerramov
, p. 66 - 67 (2007/10/03)
The reaction of aniline with 1,2,3-trichloropropane in the phase transfer catalytic system K2CO3-DMSO gives N-(2-chloroallyl)aniline as the major product.
N-Substituted Lithium 2-Lithioallylamines: New Intermediates in Synthesis
Barluenga, Jose,Foubelo, Francisco,Fananas, Francisco J.,Yus, Miguel
, p. 553 - 557 (2007/10/02)
N-Phenyl or N-benzoyl 2-halogenoallylamines (5) or (10) react successively with phenyl-lithium and lithium naphthalenide at -78 deg C to give the intermediates (4) or (11), which on reaction with electrophiles (water, deuterium oxide, dimethyl disulphide, aldehydes, ketones, or allyl bromide) yield functionalized allyl amines (6) and (12).The corresponding N-alkyl derivatives (9) afford prop-2-ynylamines (8) under the same reaction conditions.
SYNTHESIS OF INDOLES FROM N-(TRIFLUOROACETYL)-2-ANILINO ACETALS
Nordlander, J. Eric,Catalane, David B.,Kotian, Kirtivan D.,Stevens, Randall M.,Haky, Jerome E.
, p. 778 - 782 (2007/10/02)
N-(trifluoroacetyl)indoles (3) are produced in high yield from appropriately ring-substituted N-(trifluoroacetyl)-2-anilino acetals (2) in boiling trifluoroacetic acid containing excess trifluoroacetic anhydride.Mild saponification provides the free indoles nearly quantitatively.The scope of the reaction is discussed.The ring closure follows solvolytic substitution of a trifluoroacetoxy group for one of the ethoxy groups in 2.The method has been extended to cyclization of N-(trifluoroacetyl)-α-anilinoacetone in hot polyphosphoric acid followed by saponification to yield 3-methylindole.
