2- Anilino-1-methylthio

Cyclobutan 1-(1-Pentinyl)-1-thiocyanato- IV/lb, 404 Ethen l-(N-Methyl-anilino)- -methylthio- VII/4, 435/E6b/l, 108 (R-CH2-CS-NR2/H3CI) Thiobenzoesaure 4-Methyl- -dime-thylamid E5, 1221 (Cl -> Ar) Thioessigsaure Phenyl- -dimethyl-amid Ell, 242 (aus 2-Alkyliden-],3-dithio]an-l,l-dioxid)... 

Ethyl 2-ethylthio-4-chloro-5-pyrimidinecarboxylate (XXIIa), as well as the corresponding4-hydroxy-(XXIIb) and 4-amino-(XXIIIa) derivatives, possess-anti-cytogenic activity on Neurospora crassa [223, 224]. Compounds (XXIIIa, b and c) were found to inhibit the conversion of orotic acid to the uridine nucleotides [202]. Ethyl 2-methylthio-4-(halo-substituted anilino)-5-pyrimidinecarboxylates (XXIV), particularly the o-bromo- and the o-chloro- derivatives, substantially inhibit the growth of five experimental mouse tumours (Krebs-2 ascites carcinoma, Ehrlich carcinoma clone 2, leukaemia L-1210, carcinoma 755 and lymphocytic neoplasm P-288) [225]. Compounds of this type are usually prepared by the base catalysed condensation of ethoxymethylenemalonic esters or related derivatives with urea, thiourea, guanidine, or substituted amidine-type analogues [212, 225-237]. 

Methylthio-purin reagiert mit Anilin in Gegenwart von Quecksilber(II)-chlorid zu einem Komplex, dessen Zersetzung mit Schwefclwasserstoff 6-Anilino-purin (77%) ergibt ... 

Similar condensations of 5-amino-6-substituted anilino-3-methyluracils with glyoxal, diacetyl and benzil led to the corresponding 3-methyl-8-substituted phenyllumazines of which the 8-(4-chlorophenyl)- and 8-(3,5-dimethylphenyl)-3-methyllumazines showed activity against cultured Plasmodium falciparum <90AJC1449>. 5-Amino-6-methylamino- and 6-/Miydroxyethyl-2-methylthio-4(3//)pyrimidone also condense with glyoxal, diacetyl, and benzil to the corresponding 8-substituted... 

Triazin 5-[Chlor-(N-methyl-anilino)-methyl]-3-methylthio-E9c, 631 (H - CHQ—NR2)... 

Thiazol 5-Anilino-4-ethoxycar-bonyl-2-methylthio- E8b, 147 [R-NCS + ROOC-CH,-N = C(SR)2]... 

Diphenyl-2-methylthio- und 2,4,6-Triphenyl-l,3-thiazinium-perchlorat reagieren mit Hy-drazin, Benzyl- und Anilinocarbonyl-hydrazin (bei den Acyl-hydrazinen unter Abspaltung des Acyl-Restes) zu 3,5-Diphenyl-1H-pyrazol [45-68% Schmp. 200° (Methanol)]2054. 6-Alkoxycarbonyl-2,3-dihydro-l,4-thiazin verhalt sich gegeniiber Hydrazin wie das En-amin eines 3-Oxo-carbonsaure-esters und gibt so 4-(2-Anilino-ethylthio)-5(3)-hydroxy-3(5)-methyl-1 H-pyrazol1203. 

Anilino-l-cyan-2-ethoxycarbonyl-methylthio-ethenyl)-.. 686 (R - Pyridinium Schwefelkohlenstoff, Kaliumcarbonat/Methyliodid) 2- (2,2-Bis-[methylthio]-l-pyridinium- ethyl)-...- iodid687... 

Anilino-thiocarbonylamino)-4-methyl- 58 2-Arensulfonylamino- 196 5-Aroyl-2-methylthio- 132 2-(3-Arso-anilino)-4-methyl- 286 Aryl- 304... 

Cyan-2-(N-methyl-anilino)-4-methyl- 68 2-(Cyan-methyl)-4-hydroxy- 8, 10, 11 5-Cyan-2-methyl-4-phenyl- 152 5-Cyan-2-(4-methyl-phenyl)-4-trinuormethyl-a us 5-F1 uor-2-(4-methyl-phenyl)-4-trifl uor-methyl-1,3-thiazol/Kaliumcyanid 297 2-[l-Cyan-l-(methylthio-thiocarbouyl)-methyliden -4-pheny l-2,3-dihvdro- 233 5-Cyan-2-morpholino-4-phenyl- 136 2-[2-(3-Cyan-phenyl)-ethenyl]-4-isopropyl- 312... 

Amino-5(3)-anilino- 449 5-Amino-3-anilino-l-(l-anilino-2-cyan-2-ethoxy-carbonyl-ethenylazo)-4-ethoxycarbonyl- 709 5-Amino-4-anilinocarbonyl-3-methylthio- 472 3(5)-Amino-5(3)-anilino-4-ethoxycarbonyl- 599 5(3)-(2-Amino-anilino)-3(5)-phenyl- 566 5-Amino-l-arensulfonyl- 445 3(5)-Amino-4-aryl- 526 3(5)-Amino-5(3)-aryl- 469 5-Atnino-1-arylaminocarbonyl- 695 5-Amino-l-aryl-4-arylazo- 664 5-Amino-4-arylazo-l -benzolsulfonyl-3-methyl- 578 3(5)-Amino-5(3)-aryl-4-cyan- 467 5-Amino-l -aryl-4-cyan-... 

Amino-4-cyan-5(3)-(4-methyl-anilino)- 471 5-Amino-4-cyan-1 -methyl-3-phcny 1- 466 5-Amino-4-cyan-3-methylthio- 472... 

Dioxo-3-ethyl-l, 5,6,7-tetrahydro- 677 Pyrazolo[3,4-d]-l, 3-oxazin l,3-Dimethyl-4-oxo-6-(2-oxo-propyl)-dihydro- 557 1- Acyl-3-methylthio-6-oxo-l,6-dihydro- 676 2- Benzyl-6-(4-nitro-phenyl)-4-oxo-2,4-dihydro-676 4-Amino-7-chlor-phenyl- 976 2-(4-Aminosulfonyl-phenyl)-4,7-dichIor- 977 2-(4-Aminosulfonyl-phcnyl)-4,7-dihydroxy- 922 4-Anilino-7-chlor-2-(3-thienyl)- aus 4,7-DichIor-2-(3-thicnyI)- pyriclazino-[4,5-d]-l,3-thia7.ol)/Ethanol 976 7-Chlor-4-ethoxy-2-methyl- 972 7-Chlor-4-methoxy-2-phenyl- 972 7-ChIor-4-(3-pyrroIidino-propyloxy)-2-(2-thienyI)- 972... 

Reaction of 6-benzyl-3-methylthio-4-phenyl-l,2,4-triazines (200) with hydrazine gave the 4-amino-3-anilino-l,2,4-triazin-5(4//)-ones (201) (Equation (20)) <88JHC279>. 

A soln. of dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate in THF added drop wise to a stirred soln. of K-/cr/-butoxide in the same solvent at -78° under N2, a soln. of phenyl isothiocyanate in the same solvent added slowly after 30 min, stirring continued at —78° for an additional 30 min, the mixture allowed to stand at room temp, for 2 h, then quenched with water 4-ethoxycarbonyl-2-methylthio-5-anilino-thiazole. Y 90%. F.e.s. C. Alvarez-Ibarra et al.. Heterocycles 27, 2177-83 (1988). 

Stable o- and p-naphthoquinone methides leading to (316) have been obtained by a two-stage process, starting with 6-methoxy-l,3,8-tri-hydroxynaphthalene, and studies on the stability conferred on ylides by the phenylimino-group (PhN=) have led to the synthesis shown in Scheme 41 for the formation, in high yield, of the ylide (317) from 2-anilino-3-methylthio-1,4-naphthoquinone (318). 

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