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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields.
Abstract: A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.
59 citations
TL;DR: A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond.
Abstract: A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.
59 citations
TL;DR: Cyclisation d'undecatetraenes-1,3,8,10 disubstitues en derives de tetrahydro-3a,6,7,7a indane, catalysee par l'hexachloroantimoniate de tris-(bromo-4 phenyl) aminium.
Abstract: Cyclisation d'undecatetraenes-1,3,8,10 disubstitues en derives de tetrahydro-3a,6,7,7a indane, catalysee par l'hexachloroantimoniate de tris-(bromo-4 phenyl) aminium
59 citations
TL;DR: In this article, a metathesis condensation process was applied for the synthesis of double cyclic, 8-shaped poly(THF)s, which were unequivocally characterized by means of 1H NMR, SEC, and MALDI−TOF MASS techniques.
Abstract: A metathesis condensation process was applied for the synthesis of double cyclic, 8-shaped poly(THF)s. Thus, first, a cyclic poly(THF) having an allyl group, 1, was subjected to the intermolecular metathesis condensation. The bimolecular condensation reaction was found to proceed in the presence of a Grubbs catalyst, while with noticeable concurrent reactions. Alternatively, a twin-tailed tadpole, i.e., “a ring with two branches” structure, poly(THF) having tail-end allyl groups, 2, and a kyklo-telechelic poly(THF) having two allyl groups at opposite positions, 3, were prepared for the intramolecular metathesis condensation. The unimolecular reactions proceeded effectively even under dilution of the polymer concentration at 0.2 g/L to produce the corresponding 8-shaped poly(THF)s. These products were unequivocally characterized by means of 1H NMR, SEC, and MALDI−TOF MASS techniques.
59 citations
TL;DR: The demonstration of a reversible self-locking operation of 1, as in the form of 1 supersetcis-2, spontaneously retrieves the internally locked state, after the release of 2 from 1 upon cis-to-trans photochemical isomerization of ligating 2, while the backward Photochemical isomers of 2 in the presence of 1 results in switching of 1 to its externally locked state.
Abstract: Rotary host 1, composed of a ferrocene unit as a rotary module, is conformationally locked internally in apolar solvents such as benzene by a double intramolecular Zn−N coordination between the zinc porphyrin and aniline units, attached to each cyclopentadienyl (Cp) ring. Upon addition of the cis form of 1,2-bispyridylethylene (cis-2) to (+)-1 ([cis-2]/[(+)-1] = 5.0), an enantiomer of 1, the intramolecular Zn−N coordination bonds in (+)-1 are readily cleaved to form an externally locked, cyclodimeric one-to-one complex (+)-1⊃cis-2, accompanying a rotation of the ferrocene module, as visualized by CD spectroscopy. In contrast, use of trans-2, in place of cis-2, under otherwise identical conditions to the above, did not result in releasing the internal double lock of (+)-1. Such a large difference between the isomers of 2 in the affinity toward host 1, along with their capabilities of photochemical interconversion, allowed for the demonstration of a reversible self-locking operation of 1. Namely, the extern...
59 citations