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A New Route to the Imidazole-2-Thiones from 2-Thiohydantoins IMPLICATIONS in the STUDY of ERGOTHIONEINE

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A New Route to the Imidazole-2-Thiones from 2-Thiohydantoins IMPLICATIONS in the STUDY of ERGOTHIONEINE Biochem. J. (1968) 109, 209 209 Printed in Great Britain A New Route to the Imidazole-2-thiones from 2-Thiohydantoins IMPLICATIONS IN THE STUDY OF ERGOTHIONEINE BY J. E. SCOTT AND GILLIAN HENDERSON Medical Re8earch Council Rheumati8m Research Unit, Canadian Red Cro88 Ho8pital, Taplow, Maidenhead, Berk8. (Received 4 March 1968) 1. 2-Thiohydantoins are reduced by borohydrides to 4(5)-hydroxyimidazolidine- 2-thiones, which eliminate water in acid to form imidazole-2-thiones. Both steps take place in mild conditions, in high yield. A number of imidazole-2-thiones have been synthesized by this sequence of steps, with one, two or three substituents in the 1-, 3- and 4(5)-positions. 2. 4(5)-Hydroxyimidazolidine-2-thiones are am- monium pseudo-bases, giving rise to an equilibrium mixture of amino aldehyde, carbinolamine and mesomeric ammonium cationic forms. The elimination of water is suggested to be a property of the mesomeric ammonium cation. 3. The mild conditions in which imidazole-2-thiones are formed from 4(5)-hydroxy- imidazolidine-2-thiones are similar to those in which ergothioneine, a naturally occurring imidazole-2-thione of uncertain function, is normally released and measured. It is suggested that the occurrence in vivo ofa precursor to ergothioneine, in the form ofa 4(5)-hydroxyimidazolidine-2-thione, would explain many otherwise conflicting published data. Tmidazole-2-thiones are usually prepared by thiohydantoin of glucosaminic acid with sodium heating a-thiocarbamido derivatives of acetals and borohydride (Scott, 1964; Scheme 1: R = D-arabino- ketones in strong acid (the Wohl-Marckwald tetrahydroxybutyl, R' = H, R" = phenyl). The reaction). Burtles, Pyman & Roylance (1925) analogous reduction of the 3-phenyl-2-thiohydan- suggested that the acetal alkoxy groups are cleaved toin of alanine was rapid and quantitative at room before cyclization. The direct route from a-amino temperature. aldehydes is not readily available, because of the If 4(5)-hydroxyimidazolidine-2-thiones are inter- difficulty ofmaking this reactive type ofcompound. mediates in the Wohl-Marckwald synthesis, the Bullerwell & Lawson (1951), following the principle reduced products of 2-thiohydantoins ought to be of Akabori, prepared a-amino aldehydes in 8itu, by converted into imidazole-2-thiones in acid con- reduction of ac-amino acid esters with sodium ditions, and this was found to occur. Conversion amalgam in the presence of thiocyanate, but yields was rapid and quantitative, and could be followed of imidazole-2-thiones were sometimes very low. easily by spectrophotometry. The imidazole-2- No fixed procedure was discovered, and it is not a thione from the 3-phenyl-2-thiohydantoin of general method. alanine crystallized spontaneously at room tempera- OnepossibleintermediateintheWohl-Marckwald ture in pure form in 86% yield from the acidic reaction is a 4(5)-hydroxyimidazolidine-2-thione aqueous solution. This is compared with a 28% (Scheme 1), formed by the cyclization of the alde- yield from the acetal after 30min. reflux in 5N- hydothiourea, which could then dehydrate to the hydrochloric acid (Burtles et al. 1925) or 55% imidazole-2-thione. Seldom, if at all, have these (Bullerwell & Lawson, 1951) from the a-amino acid intermediates been prepared or isolated, except with ester. 2-amino-2-deoxyaldoses, which react with isothio- The ease and convenience of this preparation cyanates to give a 4(5)-hydroxyimidazolidinethione stimulated attempts to prepare other imidazole-2- (Scott, 1964; Scheme 1: R = polyhydroxyalkyl, thiones from 2-thiohydantoins, substituted in all R' = H, R' = phenyl etc.). In this context, 2-amino possible positions. The results show that mono-, di- sugars are hemiacetals analogous to those that and tri-substituted imidazole-2-thiones are con- would be produced in the hydrolysis of acetals veniently prepared in high yields by this route. according to Burtles et al. (1925). The product of Because ofthe ease ofdesulphurization ofimidazole- phenyl isothiocyanate with glucosamine could 2-thiones, a new route is opened to imidazoles in alternatively be made by reducing the phenyl- general. The mild conditions used throughout 210 J. E. SCOTT AND G. HENDERSON 1968 H OH H Co6 Ce9 . Co - .. [H+] I Ce R' H,,N-R# Ce R'f-N'l~C,N-R- *^P4E.f C.c,ig 11 11 ce 10Oc. S S M. .4Z Thiohydantoic acid 2-Thiohydantoin . BH4-/ 10 * . 10.10 vo . H H ; 1 '5 R-C-C-OH 0 C . PSv R'-N " N-R' II S [H+/ Ce O10 0 0 0 4(5)-Hydroxyimidazolidine- Co 10 t- L- C- .- 10 2-thione H H R-C C-H _IQ I IHC\N-R, ; .e3830- R-N,,C,"'5 RN II n 11 o 48C Ca S no~~~Ca a-Thiocar 0 4E° Imidazole-2-thione 'bamidoaldehyde E-4H E-4 ~ OH- H- H H H- Scheme 1. no 0_ 0 o o _ _ _ _ _ _ _ _ _ a~ ~ _. Ca co should ensure that labile groups in the molecule ,O remain intact. A preliminary account of some of this work has , been published (Scott, 1968). EXPERIMENTA] Preparation of 2-thiohydantoin8. 2-Tbiiohydantoins with- e C out substituents at N-3 were made by the general method , Ca S=4E of Johnson & Nicolet (1913), from the --aminoacid,inhigh ,0,x¢ i yield and with great convenience. WitVh th exceiDVtio of 1,3-dimethyl-2-thiohydantoin, which w,as prepared by the method of Cook & Cox (1949), 2-tIliohydantoins with or substituents at N-3 N methyl phenyl were prepared from 450.01oICe: Co-- methyl or phenyl isothiocyanate and the a-amino acid: 1 mole of amino acid in aq. 67% (v/v) pyridine, 1-1 mole of triethylamine and 1-1 mole ofisothiocyainate were incubated 10-o o o ¢X O s a for 4hr. at 370 with stirring. In some cases the amino acid o C 0 Co was not completely soluble at the outset but as the reaction t- 0~~C- ~ ~ C~ ~ j f f r- continued solution ofthe amino m~~ 10C Cee CCo acid bec*ame complete. The 4 g - - to solution was extracted three times wit,h 3vol. of benzene. e Conc. HCl (2 moles) was added to the a(queous layer, which was heated on a steam bath for 30min. axnd then cooled to 40. In many cases heating was not requir ed: conversion into the 2-thiohydantoins occurred at room temperature on leaving overnight. The solid that sepaIrated was recrystal- lized. Melting points, recrystallizing solvents and other relevant data are given in Table 1 for thoose 2-thiohydantoins that were used as starting materials forr the preparation of - Z a: X 4 10a: aauk CP4 1 4 ~~~ ~ . P the imidazole-2-thiones shown in Table 2. Ce0 Preparation of imidazole-2-thione8. All the available 16 Vol. 109 IMIDAZOLE-2-THIONES FROM 2-THIOHYDANTOINS 211 .. I I" N 0-8 -._IW * 10 4 0, 067 / 10 0-6 CO -0 6 ,.t 1 "e m *p E 0 4 oo ,di xoC V° Gc' 03 02 0.I CB4 0220 240 260 280 Wavelength (m,t) Fig. 1. Spectra (in water) of 5-methyl-2-phenyl-2-thio- 0~, 0 0 hydantoin ( -) (Emax. 16000), 5-hydroxy-4-methyl-1- cq~~~~~~~p pq p phenylimidazolidine-2-thione (-------) (emax. 17500) and 4-methyl-1-phenylimidazole-2-thione (-C-.-)(6243 7900). O , L ,0 C)g O : 2-thiohydantoins could be reduced to the 4(5)-hydroxy- 414 imidazolidine-2-thiones by LiBH4 in dioxan. The 10% (w/v) thiohydantoin in dioxan was added in .1 C) - , iM 0 c portions to a fresh 5% (w/v) suspension of LiBH4 in dioxan at 370 with stirring. About 1g. of LiBH4 was used/g. of thiohydantoin. Vigorous effervescence occurred. After 4." e- 30-60min. aq. 10% (v/v) acetic acid was added, in the ratio 4 4Z 0b 9~ ~ ~ ~~C C c 2 moles of acetic acid/mole of LiBH4. The solution was boiled for 5-10min. and then, while gently simmering, was over-neutralized to approx. pH 10 with solid Na2CO3. The solution was cooled to 4°. In many cases crude imidazole-2- thione separated and could be further purified. Some imidazole-2-thiones (e.g. imidazole-2-thione, 1-methyl- imidazole-2-thione and 1-phenylimidazole-2-thione) were more efficiently recovered by extraction with diethyl ether. An alternative procedure, which could not be used on -q 04 oq O( 2-thiohydantoins in which N-3 was unsubstituted, utilized o0 ,2 43000 NaBH4 in aqueous was Q $ cq 6i diglyme. Aq. 2% (w/v) NaBH4 aq4 cq I4 added to a diglyme solution of the thiohydantoin at room temperature with stirring. About 2-3 equiv. of NaBH4 was used/mole of thiohydantoin. The concentration of diglyme 0 ~ ~~ ~ ~ ~ was adjusted to suit the solubility of the thiohydantoin. A -4-1A considerable amount of insoluble thiohydantoin was permissible at the outset, since the intermediates were very soluble. The reaction was slower in higher concentrations of 0~~~~~~ diglyme. Gas was evolved, and after 30-120min. the P4 ~ ~ ~ solution was adjusted to pHO-5 with conc. HCI. Imidazole- 2-thione frequently began to separate in 2-3hr., especially if the diglyme concentration was low. The conversion into imidazole-2-thione could be accelerated by warming, and at 100° was usually complete in 1 min. or less. Both procedures could be monitored spectrophoto. S t Q V P4 eD4 P metrically with considerable benefit. The characteristic -^ ^4H 2-thiohydantoin peak at about 265m,t moves on reduction 212 J. E. SCOTT AND G. HENDERSON 1968 to an equally clear peak characteristic of 4(5)-hydroxy- 5% (v/v) acetic acid was added, and the precipitated boric imidazolidine-2-thiones at about 238ml. (see the examples acid was filtered off.
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