Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates

Sandler, Stanley R.

doi:10.1016/b978-0-08-092556-1.50016-6

Cited by 3 publications

(1 citation statement)

References 43 publications

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“…(A) Ammonium Tolyldithiocarbamates 2a-c. The tolyldithiocarbamates were synthesized by standard literature procedures (21). Thus, into a stirring mixture of CS2 (1.67 g, 22 mmol) and NH4OH (30%, 3 mL) was added 2.74 g (20 mmol) of 0-, m-, or p-toluidine, la-c, respectively, in a dropwise fashion.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N-(purin-8-yl)arylamines

Swenson

El‐Bayoumy

Shuie

et al. 1993

Chem. Res. Toxicol.

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Methods for direct synthesis of N-(purin-8-yl)arylamines were investigated. N-(Purin-8-yl)arylamines are adducts from reaction of electrophilic metabolites of arylamines with DNA and have not been readily available by direct synthesis. Ability to generate significant quantities of this class of DNA adduct by synthetic means would facilitate basic research in molecular toxicology. Two routes with common thiourea intermediates were developed for this purpose. In the first route, 6-hydroxy-2,4,5-triaminopyrimidine was caused to react in aqueous medium with dithiocarbamate derivatives of o-, m-, or p-toluidine to form corresponding 2,4-diamino-5-(tolylthioureido)aminopyrimidin-6-ones in 60-70% yields. The thiourea intermediates were converted to carbodiimides and isolated in 20-25% yields after treatment with HgO in dimethylformamide. The carbodiimides were cyclized at 125 degrees C in dimethylformamide under N2 for 45 h to yield N-(guanin-8-yl)(o-, m-, or p-)toluidines in 65-75% yields. In the second route, direct reaction of p-tolyl isothiocyanate with 6-hydroxy-2,4,5-triaminopyrimidine or with 4,5,6-triaminopyrimidine in dimethylformamide and triethylamine led to the formation of 2,4-diamino-5-(p-tolylthioureido)aminopyrimidin-6-one and 4,6-diamino-5-(tolylthioureido)aminopyrimidine, respectively, in 77-79% yields. Methylation of the two thiourea derivatives by methyl iodide in dimethylformamide gave the corresponding methylisothiuronium derivatives, which were isolated in 71% and 84% yields (as HI salts), respectively. Conversion of the methylisothiuronium derivatives to N-(guanin-8-yl)-p-toluidine or N-(adenin-8-yl)-p-toluidine was accomplished by heating in dimethylformamide for 5-7 h at 80-90 degrees C, in 70% and 62% yields, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Methodsmentioning

confidence: 99%

Synthesis of N-(purin-8-yl)arylamines

Swenson

El‐Bayoumy

Shuie

et al. 1993

Chem. Res. Toxicol.

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Isothiocyanato‐substituted hydrophilic polymer beads for immobilization of enzymes

Kitano

Hasegawa

Kaku

et al. 1990

J of Applied Polymer Sci

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SynopsisStyrene-glycidylmethacrylate-divinylbenzene resin beads could be converted to highly hydrophilic resin beads by acid treatment. These resin beads could be modified with isothiocyanato (NCS) groups quite easily using a Friedel-Crafts reaction and a subsequent nucleophilic reaction with KSCN. The resin beads substituted with NCS groups were useful as supports to immobilize enzymes, because they were not only hydrophilic but also bind proteins covalently. The enzymes immobilized onto the resin beads showed sufficiently high catalytic activities for a long period.

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Synthesis and transformations of stereoisomeric ethyl 2‐isothiocyanato‐1‐cyclopentanecarboxylatesm

Palkó¹,

Fülöp²,

Evanics³

et al. 2000

Journal of Heterocyclic Chem

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Ethyl vis‐ and trans‐2‐isothiocyanato‐1‐cyclopentanecarboxylates 2 and 7 were prepared by the reaction of the corresponding alicyclic ethyl 2‐amino‐1‐carboxylates and thiophosgene. The cis‐isothiocyanato compound 2 underwent ring closure with amines in one or two steps, resulting in 3‐substituted‐cis‐2‐thioxocyclopenta[d]pyrimidin‐4‐ones 3a‐g. The trans isomer 7 failed to cyclize, but gave carboxamide 8a,b or thiourea ester derivatives 9a,b.

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Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates

Cited by 3 publications

References 43 publications

Synthesis of N-(purin-8-yl)arylamines

Synthesis of N-(purin-8-yl)arylamines

Isothiocyanato‐substituted hydrophilic polymer beads for immobilization of enzymes

Synthesis and transformations of stereoisomeric ethyl 2‐isothiocyanato‐1‐cyclopentanecarboxylatesm

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