53626-84-9Relevant academic research and scientific papers
One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives
Tanyeli, Cihangir,Akhmedov, Idris M.,Yazicio?lu, Emre Y.
, p. 9627 - 9629 (2004)
We describe the preliminary results of one-pot syntheses of various N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives from 2-(2-bromoallyl)cyclohexanone and the corresponding primary amines in good yields. Aliphatic amines were directly converted to tetrahydroindoles, whereas aromatic amines needed an extra base treatment step to complete the transformation.
Tandem 5-exo-dig-5-exo-trig radical cyclization leading to a 6,5-ring fused carbobicycle possessing two contiguous quaternary carbons at the bridgehead and its adjacent positions
Nagano, Hajime,Ohtani, Yohko,Odake, Eiko,Nakagawa, Junko,Mori, Yukie,Yajima, Tomoko
, p. 338 - 339 (1999)
The tin-mediated tandem 5-exo-dig-5-exo-trig radical cyclization of dibromoacetal 4a stereoselectively gives the angular 6,5,5-ring fused tricycle 6 via spirocyclic acetal 5 in 93% yield.
Catalytic Cycloisomerization onto a Carbonyl Oxygen
Shi, Shicheng,Kuo, Jonathan L.,Chen, Tao,Norton, Jack R.
, p. 6171 - 6176 (2020)
We have found that terminal N-vinylindoles bearing cycloalkanone substituents are excellent hydrogen atom acceptors, generating α-aminyl radicals with a variety of catalysts (Co(II)/H2 or Co(III)Cl precatalysts with silane reductants). These radicals can
Vinylcyclobutanols: A composite functional group?
Trost, Barry M.,Chen, Deborah W. C.
, p. 12541 - 12554 (2007/10/03)
The effect of small strained rings on chemical reactivity was probed by the examination of the behavior of vinylcyclobutanols as terminators in cyclization reactions. The substrates were readily available by the addition of vinyllithium reagents bearing acetals as cyclization initiators to cyclobutanone. Bronsted and Lewis acids both promoted cyclization in contrast to vinylcyclopropanol terminators for which Bronsted acids failed. The products are spirocycles consisting of a cyclopentanone derived from ring expansion of the cyclobutanol and the second ring derived by attack of the terminator on the initiator. Spirocyclization to [4.5] and [4.6] systems proceeded smoothly, whereas spirocyclization to a [4.7] system failed. Attaching the cyclization termini to a preexisting ring system (whereby tricycles consisting of a fused bicycle and a spirocycle are formed) expands the scope of the cyclization to include the [4.7] ring system even at 0.01 M, a rather high concentration for such an unfavorable ring system. The diastereoselectivity generally placed the initiator substituent and the carbon-carbonyl bond of the cyclopentanone ring trans on the newly formed ring. Cyclic acetals and the free aldehyde also served as initiators. The mechanistic implications of these observations are discussed.
Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons
Mori, Miwako,Washioka, Yumiko,Urayama, Takao,Yoshiura, Kagari,Chiba, Katsumi,Ban, Yoshio
, p. 4058 - 4067 (2007/10/02)
The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.
