5-Amino-3-methylthio

Isothioharnstoff S-Methyl-N-(amino-methylthio-methylen)-E4, 1187 [(H2N-CS)2NH + (H3CO)2SOJ... 

Cyanamid [(4-Methoxy-benzyl-amino)-methylthio-methylen]-E4, 1298 [(RS)3C = N-CN + Amin]... 

Beschrieben wird femer die Cyclisierung mit Kohlenstoffdisulfid in Pyridin unter Verwendung von o-Amino-methylthio-hetarenen als Edukte z.B.140. 

Mannostatins A an B, newly discovered inhibitors of [Pg.199]

Nucleophilic reactivity of the sulfur atom has received most attention. When neutral or very acidic medium is used, the nucleophilic reactivity occurs through the exocyclic sulfur atom. Kinetic studies (110) measure this nucleophilicity- towards methyl iodide for various 3-methyl-A-4-thiazoline-2-thiones. Rate constants are 200 times greater for these compounds than for the isomeric 2-(methylthio)thiazole. Thus 3-(2-pyridyl)-A-4-thiazoline-2-thione reacts at sulfur with methyl iodide (111). Methyl substitution on the ring doubles the rate constant. This high reactivity at sulfur means that, even when an amino (112, 113) or imino group (114) occupies the 5-position of the ring, alkylation takes place on sulfiu. For the same reason, 2-acetonyi derivatives are sometimes observed as by-products in the heterocyclization reaction of dithiocarba-mates with a-haloketones (115, 116). 

The alkylthio group is replaceable by nucleophiles. The positions 7 and 4 react under mild conditions in that order the 2-alkylthio functions require more drastic treatment. Conversion of l-methyl-4-methylthiopteridin-2-one (157) into the 4-methylamino derivative (158) can be achieved by stirring with methylamine at room temperature (equation 48). The reactivity of an alkylthio group can often be further enhanced by oxidation to the corresponding sulfoxide and sulfone. Thus, reaction of l,3-dimethyl-7-methylthiolumazine (160) with m-chloroperbenzoic acid yields 7-methylsulfinyl- (161) and 7-methylsulfonyl-l,3-dimethyllumazine (162 equation 49) (82UP21601). 4-Amino-2-methylthio-7-... 

Urothione 7-Amino-2-(r,2 -dihydroxyethyl)-3-methylthio-5-oxo-5,6- dihydrothieno[3,2-g]pteridine (70)... 

Azapurine, 6-amino-synthesis, 5, 726-727 8-Azapurine, 1-deaza-synthesis, 5, 887 8-Azapurine, 3-deaza-synthesis, 5, 887 8-Azapurine, 6-methylthio-degradation, 5, 721 8-Azapurines nomenclature, 1, 36... 

BAY 94337 — see l,2,4rTriazin-5-one, 4-amino-6-t-butyl-3-methylthio- Bay region epoxides, 7, 189 Beckmann rearrangement, 7, 34 Beirut reaction, 3, 181-184 6, 407, 425 Bemegride... 

Pteridine-4,7-dione, 8-methyl-2-methylthio-oxidation, 3, 299 Pteridine-4,7-dione, 2-methylthio-reactions, 3, 296 Pteridine-6,7-dione, 2-amino-synthesis, 3, 293... 

Pteridine-7-thione, 2-amino-7-(methylthio)-4-pentyloxy-6-propionyl-alkyl substitution, 3, 301 Pteridine-7-thione, 2-amino-4-pentyloxy-methylation, 3, 299... 

Purines, N-alkyl-N-phenyl-synthesis, 5, 576 Purines, alkylthio-hydrolysis, 5, 560 Mannich reaction, 5, 536 Michael addition reactions, 5, 536 Purines, S-alkylthio-hydrolysis, 5, 560 Purines, amino-alkylation, 5, 530, 551 IR spectra, 5, 518 reactions, 5, 551-553 with diazonium ions, 5, 538 reduction, 5, 541 UV spectra, 5, 517 Purines, N-amino-synthesis, 5, 595 Purines, aminohydroxy-hydrogenation, 5, 555 reactions, 5, 555 Purines, aminooxo-reactions, 5, 557 thiation, 5, 557 Purines, bromo-synthesis, 5, 557 Purines, chloro-synthesis, 5, 573 Purines, cyano-reactions, 5, 550 Purines, dialkoxy-rearrangement, 5, 558 Purines, diazoreactions, 5, 96 Purines, dioxo-alkylation, 5, 532 Purines, N-glycosyl-, 5, 536 Purines, halo-N-alkylation, 5, 529 hydrogenolysis, 5, 562 reactions, 5, 561-562, 564 with alkoxides, 5, 563 synthesis, 5, 556 Purines, hydrazino-reactions, 5, 553 Purines, hydroxyamino-reactions, 5, 556 Purines, 8-lithiotrimethylsilyl-nucleosides alkylation, 5, 537 Purines, N-methyl-magnetic circular dichroism, 5, 523 Purines, methylthio-bromination, 5, 559 Purines, nitro-reactions, 5, 550, 551 Purines, oxo-alkylation, 5, 532 amination, 5, 557 dipole moments, 5, 522 H NMR, 5, 512 pJfa, 5, 524 reactions, 5, 556-557 with diazonium ions, 5, 538 reduction, 5, 541 thiation, 5, 557 Purines, oxohydro-IR spectra, 5, 518 Purines, selenoxo-synthesis, 5, 597 Purines, thio-acylation, 5, 559 alkylation, 5, 559 Purines, thioxo-acetylation, 5, 559... 

Pyrimido[4,5-d]pyrimidine-2,4-dione, 5-amino-7-methylthio-synthesis, 3, 364... 

Sencor — see l,2,4-Triazin-5-one, 4-amino-6-t-butyl-3-methylthio-Senecio alkaloids structure, 7, 658 Senepoxide, 7, 192 Senkirkine conformation, 7, 703 structure, 7, 658 Sensitizing dyes... 

The / -(methylthio)phenyl ester has been prepared from an A-protected amino acid and 4-CH3SC6H4OH (DCC, CH2CI2, 0°, 1 h 20°, 12 h, 60-70% yield). The p-(methylthio)phenyl ester serves as an unactivated ester that is activated on oxidation to the sulfone (H2O2, AcOH, 20°, 12 h, 60-80% yield), which then serves as an activated ester in peptide synthesis. ... 

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