Synthesis acyl isothiocyanates

Wilson LJ, Klopfenstein SR, Li M. A traceless linker approach to the solid phase synthesis of substituted guanidines utilizing a novel acyl isothiocyanate resin. Tetrahedron Lett 1999 40 3999 -002. 

Wilson, L. J. Lin, M. A Traceless Linker Approach to the Solid Phase Synthesis of Substituted Guanidines Utilizing a Novel Acyl Isothiocyanate Resin, Tetrahedron Lett. 1999, 40, 3999-4002. 

Alkyl (or acyl) isothiocyanates have proved to be useful intermediates for thioxopurine synthesis and can also be used to produce guanine derivatives. Methyl isothiocyanate and... 

Dihydro-1,3-oxazines (398) are cyclic intermediates in the synthesis of a-amino-y-oxo acid esters by reaction of acyliminoacetates with enamines derived from six-membered ketones . Sulfur-containing heterocycloadducts 399 and 400 have been prepared by [4 -I- 2] cycloaddition of enamines to heterocumulenes like thioacyl isocyanates and acyl isothiocyanates . 

While exploring the synthesis of A iS -heterocycles using heterocumulenes, such as the acyl isothiocyanates ( ), we discovered weak herbicidal activity for 3-(3-chlorophenyl)-2-(iV-ethoxycarbonylimino)-5-methylene-l,3-thiazolidine,... 

Reviews cover the topics alkynethiolates in synthesis " oxygen-exchange reactions of sulphoxides sulphonyldiazomethanes C—S bond cleavage acyl isothiocyanates radical reactions of sulphur compounds addition of sulphenyl halides to olefins " sulphenamidcs mercaptoethylation of amines sulphur as a chiral centre " stereochemistry of S and S " compounds " reductive cleavage of sulphides, synthetic uses of alkene- and alkyne-thiolates, and thio-Claisen rearrangements nucleophilic displacements at sulphur in disulphides aromatic... 

The classical, Fischer7 synthesis of sugar isothiocyanates involves treatment of an acylated glycosyl halide with an inorganic thiocyanate in a polar solvent. Depending on the reactivity of the halide and the reaction conditions, either a thiocyanate or an isothiocyanate is formed directly. 

The schemes presented below also illustrate the synthesis of various amides of substituted quinoline-and quinolonecarboxylic acids 212-214 by the reaction of isatins 7, 9, 54, and 180 with amides 215 [179], acylated amino acids 216 and isothiocyanates [182], and enamines 217 [183],... 

The availability of amino-substituted furazans, both by direct synthesis from aminogly-oximes and via Hofmann degradation of the corresponding carboxamides, allows urea, thiourea, imino and acylamido derivatives, for example, to be prepared by reaction with isocyanates, isothiocyanates, aldehydes and acyl halides, respectively (73JPR791, 77JCS(P1)1616). Alkoxy and acyloxy derivatives are likewise formed from hydroxyfurazans (79JHC689). 

Pyrroles 779 and 781 were regioselectively acylated with ethoxycarbonyl isothiocyanate, affording acylated thioamides 780 and 782, respectively, as intermediates in the synthesis of pyrroloamidines, guanidine bioisostere analogs (Equations 184 and 185) <2001JME1217>. 

Suitably functionalized phenyl isothiocyanates (e.g. 127) have been used as starting materials for the synthesis of this fused heterocyclic system the rest of the skeleton is provided by acid hydrazides [74JOC3506 75GEP(O)2509843 79H1I71], The intermediate l-acyl-4-arylthiosemi-carbazides (128) and 3-mercapto-1,2,4-triazoles (129) underwent base-catalyzed cyclization to ],2,4-triazolo[3,4-a]l,3-benzothiazoles 130. 

Burke TR Jr, Jacobson AE, Rice KC, et al. Probes for narcotic receptor mediated phenomena. 12. c/s-( + )-3-Methylfentanyl isothiocyanate, a potent site-directed acylating agent for 5 opioid receptors. Synthesis, absolute configuration, and receptor enantioselectivity. J Med Chem 1986 29 1087-1093. 

A new synthesis of -acylated glycosylamines and a transformation of the products into glycosyl isothiocyanates and thence N,N-di-glycosylthioureas have been reported (Scheme 1). Other N-... 

In addition to the general procedure iUusIrated by Eq. (2.182), another route has been employed for the synthesis of metal alkoxides (and particularly analogous siloxides) by the reaction of metal alkoxides with esters (and silyl esters) (Section 4.3). Further, the reactions of metal alkoxides with acyl halides (or hydrogen halides) and unsaturated substrates such as CO, CO2, CS2, organic-isocyanates and isothiocyanates, chloral, etc. have been utilized for the preparation of haUde-alkoxides (Section 4.11) and interesting insertion products (Section 4.12), respectively. 

Functionalized terpyridines can be created to contain a variety of binding and catalytic functional groups (15). Bromomethyl derivatives can be reacted with the sodium salts of alcohols to form ethers, or reacted with the sodium salts of amines to form substituted amines. Each sodium salt was formed by reaction with sodium hydride. Gabriel synthesis leads to the creation of an aminomethyl derivative, which can be converted into amide with acyl chlorides, ureas with isocyanates, or thioureas with isothiocyanates. Terpyridine-5-carboxylic acid is converted to the acyl chloride with thionyl chloride and can be coupled with a variety of amines to form amide derivatives. 

Alkyl and acyl thiocyanates and isothiocyanates are prepared in good yields from the corresponding halides by use of polymer-supported reagents, and a convenient approach to the synthesis of dialkylaminoalkyl isothiocyanates ... 

An improved preparation of carbonyl di-isothiocyanate has been reported and the synthesis of 2-alkyl-4-arylallophanoyl selenocyanates, an almost unknown class of acyl selenocyanates, has been published. ... 

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