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[交流] 求助合成方法

4-甲基噻唑；
4-methylthiazole；
CAS：693-95-8

[ Last edited by zzgyb on 2009-1-17 at 09:23 ]

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Comparisons of the structures of thiazole and isoquinoline.    Erlenmeyer, H.; Baumann, H.; Sorkin, E. Helvetica Chimica Acta  (1948),  31  1978-93.  CODEN: HCACAV  ISSN: 0018-019X.  Journal  written in German. CAN 43:19925 AN 1949:19925 CAPLUS

Abstract

To test the hypothesis of the structural similarity of the thiazole and isoquinoline rings, 4-methylthiazole and 3-methylquinoline were condensed with BzH, giving phenyl-(4-methyl-2-thiazolyl)carbinol and 3-styrylisoquinoline, and showing dissimilarity of the C.sbd.N.sbd.C groups in the 2 rings.  4-Methylthiazole (I) heated 18 hrs. at 160-5?with BzH and fused ZnCl2 in a closed tube gave a black mixt. from which were isolated the double salt of I, C8H10N2S2.ZnCl2, m. 185-6? unreacted I, 4.3% 2-benzyl-4-methylthiazole (II), b14 150?(picrate, m. 115-16? picrolonate, m. 142?, and 0.98% phenyl(4-methyl-2-thiazolyl)carbinol (III), m. 96?(phenylurethan, m. 154-5?.  II was prepd. in 79% yield by condensing ClCH2Ac with PhCH2CSNH2 to prove its structure.  PhCH (OBz)CO2H heated in an autoclave 12 hrs. at 60?with H2S and Et2NH gave 70% of the corresponding thio amide, m. 139? which with ClCH2Ac gave 22% III for structure proof.  Condensation of I with BzH without ZnCl2 gave 6.65% III and a small amt. of II, while a similar reaction in Ac2O gave PhCH(OAc)2 and 8.1% III acetate, b22 198-202? m. 129-30? easily sapond. to III.  The products of the condensation of I.MeI and BzH could not be identified.  After refluxing BzH with 3-methylisoquinoline (IV) and ZnCl2 for a week at 160-5? the double salt of IV, C20H18N2.ZnCl2, m. 170-240? 3% 3-styrylisoquinoline (V), m. 155.5?(picrate, m. 258-9?, and iso-3-styrylisoqunoline, m. 148? were isolated.  Bromination of IV with N-bromosuccinimide in CCl4 and Bz2O2, best in sunlight, gave 20-60% 3-(bromomethyl)isoquinoline (VI), m. 104-5? solidifies at a higher temp., decomp. 270-325? which was dissolved in alc. and dropped into boiling aq. KCN to give 40-73% of 3-(cyanomethyl)isoquinoline, m. 49.5-50? condensed with BzH and NaOEt to a-3-isoquinolylcinnamonitrile, m. 194? which when heated 12 hrs. at 130?with concd. HCl in a closed tube gave 91% V.HCl, m. 202-5?  IV.MeI, m. 218-19? with p-Me2NC6H4CHO and a few drops of piperidine in abs. alc.
gave 8.5% (28% without alc.) red crystals of 3-(p-dimethylaminostyryl)isoquinoline-MeI, m. 290-1? which at 300?sublimed to give 87% 3-(p-dimethylaminostyryl)isoquinoline, m. 201-2? picrate, m. 219-20?  Heating IV.MeI with BzH and piperidine to 170?gave 29% V.MeI, m. 300-2? which was converted to V by heating to 200-20?and sublimation.  3-Isoquinoline carboxaldehyde-p-dimethylaminoanil methiodide, m. 251-2? was formed by refluxing p-ONC6H4NMe2 with IV.  Irradiation of V in C6H6 with ultraviolet light for 3 days gave 2 dimeric cyclobutane derivs. of V, m. 282-4?and 189-92? and 3 other unidentified fractions.  IV.MeI with K3[Fe(CN)6] in 2 N NaOH at 0?gave on extn. with CHCl3 2,3-dimethyl-1(2H)-isoquinolone as an oil which was dissolved in PhOMe and added to PhCH2MgCl in boiling PhOMe; decompn. of the product with dil. H2SO4 and addn. of KI gave after vacuum sublimation 1-benzyl-3-methylisoquinoline-MeI, m. 177-9?  The residue contained 1-benzyl-3-methylisoquinoline as an oil; picrate, m. 190-1?  Heating VI with AcOAg in glacial AcOH at 100?gave 90% 3-(acetoxymethyl)isoquinoline, m. 53-4? converted to 3-(hydroxymethyl)isoquinoline, m. 81? with alc. KOH at 25?

_
Journal of Organic Chemistry, 58(12), 3407-10; 1993
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