Synthesis of indoles via amidoselenation

The reaction of 2-styrylacetanilides (2) with N-phenylselenosuccinimide affords 1-N-acetyl-2-phenyl-3-phenylselenoindoles (3) and 1-N-acetyl-2-phenylindoles (4). The reaction of 2-vinylacetanilides (5) with phenylselenenyl bromide proceeds to form indoles via an intramolecular amidoselenation.

[1]  J. Stille,et al.  Palladium-catalyzed synthesis of 2-substituted indoles , 1989 .

[2]  S. Murakami,et al.  A regiocontrolled synthesis of substituted indoles by palladium‐catalyzed coupling of 2‐bromonitrobenzenes and 2‐bromoacetanilides , 1989 .

[3]  V. Birss,et al.  Study of the reductive cleavage of selenides with nickel boride. A convenient deselenization procedure , 1988 .

[4]  K. Terao,et al.  Organoselenium-induced cyclization of olefinic imidates and amides: selective synthesis of lactams or iminolactones , 1987 .

[5]  K. Terao,et al.  Intramolecular amidoselenation of N-alkenyl amides: formation of nitrogen heterocycles , 1986 .

[6]  T. Itahara.  Arylation of aromatic heterocycles with arenes and palladium(II) acetate , 1985 .

[7]  M. Kocór,et al.  Synthesis of steroid 24,20-lactones by means of phenylselenolactonization , 1985 .

[8]  K. Terao,et al.  INTRAMOLECULAR AMIDOSELENATION LEADING TO LACTAMS BY THE REACTION OF N-ALKYLALKENAMIDES WITH BENZENESELENENYL CHLORIDE' , 1984 .

[9]  R. Webb,et al.  Ureidoallylation of double bonds , 1983 .

[10]  S. Raucher,et al.  Synthesis of substituted indoles via Meerwein arylation , 1983 .

[11]  A. Toshimitsu,et al.  Amidoselenation of olefins and its utilization for synthesis of allylic amides , 1981 .

[12]  W. Kiel,et al.  Cyclofunctionalization of olefinic urethanes using benzeneselenenyl chloride in the presence of silica gel: a general route to nitrogen heterocycles , 1980 .

[13]  L. Sydnes,et al.  Photochemical synthesis. Conversion of o-vinylthioanilides to quinolines , 1980 .

[14]  K. Sharpless,et al.  Conversion of allylic phenylselenides to the rearranged allylic chlorides by N-chlorosuccinimide. Mechanism of selenium-catalyzed allylic chlorination of .beta.-pinene , 1979 .

[15]  K. Nicolaou,et al.  N-Phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). Two versatile carriers of the phenylseleno group. Oxyselenation of olefins and a selenium-based macrolide synthesis , 1979 .

[16]  H. Reich,et al.  Organoselenium chemistry. Conversion of ketones to enones by selenoxide syn elimination , 1975 .