5-Acyl-4-alkylthio

Durch Umsetzung mit Nitroso-Verbindungen (z. B. Nitrosylchlorid, Nitrosobenzol) erhalt man aus l-Alkylamino-l-alkylthio-3-oxo-l-alkenen 5-Acyl-4-alkylthio-imidazole2SS. Mit Nitrosylchlorid verlauft die Reaktion iiber die entsprechenden a-Acyl-oxime als Zwischenpro-dukte, die isoliert und in einem getrennten Schritt cyclisiert werden konnen. 

Arylthioimidazoles can be made in high yields when thiophenates react with At-(l-cyanoalkyl) alkylidene A -oxides. Alkyl and aralkyl thiolates, however, react much less readily (see Section 2.1.1 and Scheme 2.1.10). Imidazole-4-thioethers can be made in a general reaction between nitriles and a range of isocyanides which are susceptible to o -metallation (see Section 4.2, Scheme 4.2.2 and Table 4.2.1). Oxoketene acetals bearing alkylthio substituents react with nitrosoaromatics to give 5-acyl-4-alkylthio-l-arylimidazoles in moderate to good yields (see Section 3.2 and Scheme 3.2.5). 

In vergleichbarer Weise lassen sich enolisierbare a-Thiocyanat-/ -dicarbonyl-Verbindungen mit sich selbst zu 5-Acyl-4-alkylthio-2-amino-l,3-thiazolen umsetzen1018. Im Verlaufe der Reaktion wird eine der beiden Carbonyl-Einheiten abgespalten. 

Treatment of 2-mercaptoimidazoles 33 with a-halo ketones gives 2-(acyl-alkylthio)-imidazoles 34, which can be cyclized to substituted imidazo[2,l-fejthiazoles 35 [86HC(46)77]. A one-step synthesis from 33 with a-halo ketones is also successful. 

Vinyl chloride,29 vinyl acetate,30 oc-nitro olefins,31 and azlactones32 also add alkanethiols. The reaction of azlactones is accompanied by ring fission to yield V-acyl / -alkylthio oc-amino thioesters, this being a good preparative route to such compounds ... 

Acyl-(alkylthio-methylen)-iminium-Salze mit a — CH-Bindungen im Acyl-Rest cyclisieren bei Anwesenheit von Basen zu /J-Lactamen758,760 762 z.B. ... 

It is estimated that mote than 25 x 10 different potentially toxic OP esters can be made using Schrader s classic (27) formula for effective phosphorylating agents, (39), where R and are short-chain alkyl, alkoxy, alkylthio, or alkylamino groups, and X is a displaceable moiety with a high energy P-bond such as E or acyl anhydride, and the pentavalent phosphoms atom is bonded to oxygen or sulfur. 

Azete, trisdimethylamino-isolation, 7, 278 Azetes, 7, 237-284, 278-284 benzo fused, 7, 278 benzodiazepine fused applications, 7, 284 fused ring, 7, 341-362 structure, 7, 360 2,3-naphtho fusion, 7, 278 reactivity, 7, 279 structure, 7, 278 synthesis, 7, 282-283 Azetidine, acylring expansion, 7, 241 synthesis, 7, 246 Azetidine, 3-acyl-irradiation, 7, 239 synthesis, 7, 246 Azetidine, N-acyl-synthesis, 7, 245 Azetidine, alkyl-synthesis, 7, 246 Azetidine, 3-alkylthio-synthesis, 7, 246 Azetidine, 3-amino-synthesis, 7, 246 Azetidine, N-amino-oxidation, 7, 241 synthesis, 7, 246 Azetidine, aryl-synthesis, 7, 246... 

Benzo[6]thiophene, 2-acetyl-3-hydroxy-synthesis, 4, 892 Benzo[6]thiophene, 2-acyl-synthesis, 4, 918 Benzo[6]thiophene, 3-acyl-synthesis, 4, 918- 19 Benzo[6]thiophene, acylamino-synthesis, 4, 815 Benzo[6]thiophene, alkenyl-synthesis, 4, 917 Benzo[6]thiophene, 2-alkoxy-synthesis, 4, 929 Benzo[6]thiophene, 3-alkoxy-synthesis, 4, 929 Benzo[6]thiophene, 4-alkoxy-synthesis, 4, 930 Benzo[6]thiophene, 2-alkyl-synthesis, 4, 877-878 Benzo[6]thiophene, 2-alkylthio-synthesis, 4, 931 Benzo[6]thiophene, 2-amino-diazotization, 4, 810 reactivity, 4, 797 stability, 4, 810 synthesis, 4, 869, 924-925 tautomerism, 4, 38 Benzo[6]thiophene, 3-amino-cycloaddition reactions, 4, 68 synthesis, 4, 109, 881, 925 Benzo[6]thiophene, 4-amino-synthesis, 4, 925 Benzo[6]thiophene, 5-amino-synthesis, 4, 925 Benzo[6]thiophene, 7-amino-synthesis, 4, 925 Benzo[6]thiophene, 3-t-amyl-synthesis, 4, 915 Benzo[6]thiophene, 2-aryl-synthesis, 4, 881... 

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... 

Pyridazine, 3-alkylidene-2,3-dihydro-synthesis, 3, 28 Pyridazine, alkylthio-synthesis, 3, 27 Pyridazine, 3-alkynyl-synthesis, 3, 28 Pyridazine, amino-acylation, 3, 35 diazotization, 3, 35 reaction... 

Alkyl-3-acyl- 291 3-Alkylthio-2-oxo-2,3-dihydro- 446 (2-Amino-athyl)- 79 3-(2-Amino-athyl)- 242... 

The reactions of Meldrum s acid (421) and acyl isothiocyanates in DMSO in the presence of lithium hydride at ambient temperature for 2-3 hr gave the lithium salts (457), which were alkylated by treatment with alkyl halide for 5 hr to afford isopropylidene (acylamino)(alkylthio)methy-lenemalonates (458) in 20-90% yields (87ZC68). 

Bei der Umsetzung von Carbonsaure-hydraziden mit Schwefelkoblenstoff und Alkylhalogeni-den erhalt man l-Acyl-2-(alkylthio-thiocarbonyl)-hydrazine197. Diese cyclisieren unter Alkan-thiol-Abspaltung, z.B. thermisch zu 2-Mercapto-l,3,4-oxadiazolen (vgl. S. 544). Praparativ bietet diese Methode gegeniiber der Cyclisierung von Carbonsaure-hydraziden mit Schwefelkohlenstoff keine Vorteile. 

Alkylthio-5-amino-l,2,4-thiadiazoles are generally insoluble in acids and alkalis, and resist desulfurization by alkaline sodium plum-bite.132 The higher members are Bomewhat sensitive to hydrolysis85,90 the 3-phenylthio homolog is slowly destroyed by concentrated alkali, but its stability is much increased by acylation.85... 

Alkylthio- 5-amino-l,2,4-thiadiazoles and homologs Acyl derivatives thereof... 

Other 7- substituents that have been introduced include the dialkylamino, acetamido, hydroxy, alkoxy and alkylthio groups (B-71MI11209). Acylation of the 7-amino group by heterocycles such as cyanuric chloride and its derivatives was inevitable, as was incorporation of a 7-triazole substitution pattern by diazotization of the 7-amino group and o-coupling with 2-naphthylamine followed by triazolization (94). 

Pteridine, 6-alkylthio-2,4-diamino-reactivity, 3, 299 Pteridine, 2-amino-acylation, 3, 295 hydrolysis, 3, 293, 294 Michael addition reactions, 3, 279, 288 structure, 3, 267 Pteridine, 4-amino-acylation, 3, 295 hydrolysis, 3, 293, 294 3-oxide... 

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