294190-48-0Relevant academic research and scientific papers
Copper(II)chloride-mediated cyclization reaction of N-alkoxy- orthoalkynylbenzamides
Jithunsa, Manita,Ueda, Masafumi,Miyata, Okiko
supporting information; experimental part, p. 518 - 521 (2011/04/16)
A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.
Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands
Fang, Jing,Akwabi-Ameyaw, Adwoa,Britton, Jonathan E.,Katamreddy, Subba R.,Navas III, Frank,Miller, Aaron B.,Williams, Shawn P.,Gray, David W.,Orband-Miller, Lisa A.,Shearin, Jean,Heyer, Dennis
scheme or table, p. 5075 - 5077 (2009/05/07)
A series of estrogen receptor ligands based on a 3-alkyl naphthalene scaffold was synthesized using an intramolecular enolate-alkyne cycloaromatization as the key step. Several of these compounds bearing a C6-OH group were shown to be high affinity ligand
CHEMICAL COMPOUNDS
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Page/Page column 91, (2010/02/15)
The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel naphthalene compounds that are particularly useful for selective estrogen receptor modulation.
Oxyanion-Accelerated C2-C6 Cyclization of Benzannulated Enyne-allenes
Brunette, Steven R.,Lipton, Mark A.
, p. 5114 - 5119 (2007/10/03)
The cyclization of oxyanion-substituted, benzannulated enyne-allenes was found to proceed rapidly and efficiently at room temperature, producing substituted indanones and fluorenones through a C2-C6 cyclization pathway. These reactions bear close resemblance to thermal C2-C6 cyclizations of enyne-allenes previously reported by Schmittel and others, though the oxyanion-substituted cases cyclize far more rapidly, and stand in noteworthy contrast to the C2-C7 (Myers) cyclization of (Z)-1,2,4-heptatrien-6-yne, the parent enyne-allene. The rate of reaction was found to be sensitive to the size of the alkyne and allene substituents, though the electronic effects of substitution are not known. The acceleration imparted by the oxyanion substituent is consistent with the electronic stabilization of a proposed diradicaloid transition state for the C2-C6 cyclization, but the available evidence does not permit the distinction between concerted and stepwise mechanisms. Studies are ongoing to further elucidate the mechanism and expand the scope of these transformations.
