258497-77-7Relevant academic research and scientific papers
Structures of three new (phenylsulfonyl)indole derivatives
Jasinski, Jerry P.,Rinderspacher, Alison,Gribble, Gordon W.
experimental part, p. 40 - 47 (2010/03/04)
Three new 1-(phenylsulfonyl)indole derivatives, 3-acetyl-2-ethyl-1- (phenylsulfonyl)indole, (I), 2-benzyl-1-(phenylsulfonyl)indole, (II), and 3-trimethylsilylethynyl-1-(phenylsulfonyl)indole, (III), have been synthesized and their crystal structures determined by single crystal X-ray crystallography. (I), C18H17NO3S, is triclinic with space group P-1 and cell constants: a = 8.6129(2) A, b = 8.8366(2) A, c = 11.0108(2) A, α = 72.7920(1)°, β = 75.0120(1)°, γ = 77.2550(1)°, V = 763.79(3) A3 and Z = 2. (II), C 21H17NO2S, is monoclinic with space group P21/n and cell constants: a = 10.8355(18) A, b = 10.6987(19) A, c = 14.472(3) A, β = 75.0120(1), V = 1675.2(5) A3 and Z = 4. (III), C19H19NO2SSi, is monoclinic with, space group P21/c and cell constants: a = 12.9596(1) A, b = 10.543(3) A, c = 13.543(2) A, β = 93.58°, V = 1846.8(6) A3 and Z = 4. All three have the same (phenylsulfonyl)indole skeleton with different ligands attached to the 2- and 3-sites of the indole ring. The angle between the mean planes of the indole and benzyl groups is 76.9(6)° (I), 82.9(3)° (II), 89.6(2)° (III) and between the sulfonyl group with the indole and benzyl rings is 61.2(9)° (I), 59.0((5)° (II), 51.5(6)°, 42.5(8)° (III) and 51.5(6)°(I), 44.3(8)° (II), 47.2(8)° (III), respectively. In addition to the ligand substitutions, weak intermolecular C-H???O hydrogen bond interactions and π stacking interactions between the π orbitals of nearby indole and phenyl rings influence these twist angles. Comparison to a MOPAC AM1 computational calculation supports these observations.
Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine
Tanaka, Katsunori,Kobayashi, Toyoharu,Mori, Hajime,Katsumura, Shigeo
, p. 5906 - 5925 (2007/10/03)
The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-l-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.
Synthesis of β- and γ-carbolines and their N-oxides from 2(or 3)- ethynylindole-3(or 2)-carbaldehydes
Sakamoto, Takao,Numata, Atsushi,Saitoh, Hironori,Kondo, Yoshinori
, p. 1740 - 1743 (2007/10/03)
Isoquinoline-type carbolines i.e. β-, and γ-carbolines and their N- oxides were synthesized from 2(or 3)ethynylindole-3(or 2)-carbaldehydes, which were synthesized by electrophilic substitution with dichloromethyl methyl ether in the presence of titanium
