- A new application of the mild thiolation concept for an efficient three-step synthesis of 2-cyanobenzothiazoles: A new approach to Firefly-luciferin precursors
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An easy, low cost and upscalable three-step synthesis of Firefly luciferin precursors is presented. The 6-alkoxy-2-cyano-benzothiazoles (1) were synthesized starting from easily available O-alkylated 4-aminophenoles (2) via a mild thiolation, Jacobsen cyclization and dehydratization sequence.
- Wuerfel, Hendryk,Weiss, Dieter,Beckert, Rainer,Guether, Angelika
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experimental part
p. 9 - 16
(2012/07/01)
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- New approach to the synthesis of 2-carbamoylbenzothiazoles
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The reactions of substituted anilines with chloroacetamide and sulfur in the presence of triethylamine afforded monothiooxamides. When treated with K3Fe(CN)6, the latter underwent cyclization to form 2-carbamoyIbenzothiazoles. The reactions were accompanied by the formation of the corresponding thiooxanilic acids, which also underwent cyclization to form benzothiazole-2-carboxylic acids.
- Yarovenko, V. N.,Stoyanovich, F. M.,Zolotarskaya, O. Yu.,Chernoburova, E. I.,Zararzin, I. V.,Krayushkin, M. M.
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p. 144 - 147
(2007/10/03)
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- Some chemistry of 4,5-dichloro-1,2,3-dithiazolium chloride and its derivatives
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4,5-Dichloro-1,2,3-dithiazolium chloride 1 reacts with fluoroanilines (see Table 1) to give the iminodithiazoles 5 in very high yield.Thermolysis of the latter gave the corresponding 2-cyanobenzothiazoles 6 together, in some cases, with the cyanoimidoyl chlorides 7.This reaction sequence provides modest yields of 2-cyanobenzothiazoles from the corresponding aniline, in two steps.Treatment of the iminodithiazoles with m-chloroperbenzoic acid in dichloromethane at or below room temperature opened the heterocyclic ring to give the N-arylcyanothioformamides (e.g. 8 --> 10), except for the p-nitrophenyl compound which gave p-nitrophenyl isothiocyanate 14 in high yield.
- Besson, Thierry,Rees, Charles W.
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p. 1659 - 1662
(2007/10/02)
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