α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. III. A Novel Synthesis of α-Amino Ketones and α-Amino Aldehydes by Aminolysis of α,β-Epoxy Sulfoxides
- 1 February 1986
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 59 (2) , 457-463
- https://doi.org/10.1246/bcsj.59.457
Abstract
Aminolysis of α,β-epoxy sulfoxides, easily prepared from 1-chloroalkyl phenyl sulfoxides or chloromethyl phenyl sulfoxide and carbonyl compounds, with alkyl- or arylamines afforded α-amino ketones or α-amino aldehydes in good yields. Treatment of thus obtained α-arylamino ketones with weak Lewis acid led to 2,3-disubstituted indoles.Keywords
This publication has 25 references indexed in Scilit:
- α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. II. A Novel Synthesis of α-Sulfenylated Ketones and α-Sulfenylated Aldehydes from α,β-Epoxy SulfoxidesBulletin of the Chemical Society of Japan, 1985
- 2-Formylation of 3-arylindolesTetrahedron Letters, 1985
- Synthesis of α-aminoketones via selective reduction of acyl cyanidesTetrahedron Letters, 1984
- Synthesen von 2-AnilinocyclopentanonenMonatshefte für Chemie / Chemical Monthly, 1976
- Aroylmethylamine synthesis by Stephen reduction of aroyl cyanidesThe Journal of Organic Chemistry, 1972
- The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)Chemical Reviews, 1964
- Epoxy Ethers. XIX. Reaction of 1,2-Epoxy-1-methoxy-2-methyl-1-phenylpropane with AminesThe Journal of Organic Chemistry, 1962
- Reactions of Amines. V. Synthesis of α-Amino Ketones1,2Journal of the American Chemical Society, 1960
- Synthesis of Tetrahydrocarbazoles and Carbazoles by the Bischler Reaction1,2The Journal of Organic Chemistry, 1959
- The Acetylcholinesterase Surface. VI. Further Studies with Cyclic Isomers as Inhibitors and Substrates1,2Journal of the American Chemical Society, 1956