158072-90-3Relevant academic research and scientific papers
Synthesis of 3-arylindole-2-carboxylates via copper-catalyzed hydroarylation of o-nitrophenyl-substituted alkynoates and subsequent cadogan cyclization
Yamamoto, Yoshihiko,Yamada, Satoshi,Nishiyama, Hisao
, p. 701 - 706 (2011/05/08)
A two-step route to biologically important 3-arylindole-2-carboxylic esters has been successfully established: o-nitrophenyl-substituted alkynoates underwent copper-catalyzed hydroarylation in the presence of commercially available arylboronic acids to afford 3,3-diarylacrylates, which were then converted to indolecarboxylates via a modified Cadogan cyclization using a molybdenum catalyst and triphenylphosphine. Copyright
Stereoselective synthesis of unsymmetrical β,β-diarylacrylates by a heck-matsuda reaction: Versatile building blocks for asymmetric synthesis of β,β-diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro- quinolin-2-one and formal synthesis of (-)-indatraline
Taylor, Jason G.,Correia, Carlos Roque D.
, p. 857 - 869 (2011/04/18)
β,β-Disubstituted R,β-unsaturated esters may serve as valuable derivatives for the preparation of other highly functionalized systems found in many natural products and marketed drugs. The stereoselective synthesis of unsymmetrical β,β-diarylacrylate compounds possessing two similar aromatic groups remains a substantial challenge. A simple and convenient stereoselective protocol for the preparation of β,β- disubstituted acrylates via a Heck-Matsuda reaction is reported. Good to high yields were accomplished by a "ligand-free" Pd-catalyzed arylation reaction of cinnamate esters with arenediazonium tetrafluoroborates. Both electron-deficient and electron-rich arenediazonium salts could be employed as arylating reagents, and cinnamate esters were generally more reactive when substituted with an electron-donating group. The overall methodology is highly stereoselective, and this attribute was taken advantage of in the asymmetric Cu-catalyzed 1,4 reduction reaction to provide β,β-diarylpropanoates in high enantioselectivities. The synthesis of a 3-aryl indole and a chiral 4-aryl-2-quinolone from β,β-diarylacrylates was achieved by cyclization in the presence of a diphosphine ligated CuH catalyst. A convenient route for the asymmetric formal synthesis of the psychoactive compound (-)-Indatraline is also presented.
Synthesis of substituted indoles from 2-azidoacrylates and ortho-silyl aryltriflates
Hong, Deng,Chen, Zhengbo,Lin, Xufeng,Wang, Yanguang
supporting information; experimental part, p. 4608 - 4611 (2010/12/18)
2-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.
ENDOTHELIN RECEPTOR ANTAGONISTS
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, (2008/06/13)
Indole derivatives of formula (1) wherein the substituents are defined herein are disclosed. The compounds are useful in methods of antagonizing endothelin receptors, treating hypertension, treating renal failure and treating cerebrovascular disease. Pharmaceutical compositions are also disclosed.
