Hypervalent Iodine in Organic Synthesis: One Pot Facile Syntheses of α-Thiocyanatoacetophenones, 2-Hydroxy-, and 2-Mercapto-4-arylthiazoles Using [Hydroxy(tosyloxy)iodo]benzene
- 1 May 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (10) , 1455-1462
- https://doi.org/10.1080/00397919308011236
Abstract
Hypervalent iodine oxidation of acetophenones (1a-1e) with [hydroxy(tosyloxy)iodo]benzene, followed by treatment with potassium thiocyanate offers a new facile synthesis of corresponding α-thiocyanatoacetophenones (3a-3e). Cyclization of 3a-3e, thus generated in situ, using AcOH/H2O and H2NC(S)NH2/HCl provides one pot facile syntheses of 2-hydroxy-, and 2-mercapto-4-arylthiazoles (4 & 5) respectively.Keywords
This publication has 7 references indexed in Scilit:
- Hypervalent iodine in the synthesis of bridgehead heterocycles: novel and facile syntheses of 3-substituted-5,6-dihydroimidazo[2,1-b]thiazoles and 3-phenylthiazolo[3,2-a]benzimidazole from acetophenones using [hydroxy(tosyloxy)iodo]benzeneJournal of the Chemical Society, Perkin Transactions 1, 1992
- A New Synthesis of 2-Aroylcoumaran-3-ones by Hypervalent Iodine Oxidation of 2-Acetyl-phenyl Benzoates Using [Hydroxy(tosyloxy)iodo]benzeneSynthesis, 1992
- [Hydroxy(organosulfonyloxy)iodo]arenes in Organic SynthesisSynlett, 1990
- One-step .alpha.-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzeneThe Journal of Organic Chemistry, 1982
- Hypervalent organoiodine. Crystal structure of phenylhydroxytosyloxyiodineThe Journal of Organic Chemistry, 1976
- Aminoalkyl Ethers of 2-Hydroxythiazoles.Acta Chemica Scandinavica, 1953
- The Syntheses of 2-Thio-4-arylthiazolinesJournal of the American Chemical Society, 1939