53626-84-9Relevant articles and documents
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.
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.