Synthesis of thiazoles and imidazoles from isothiocyanates and tosylmethyl isocyanide. Base‐induced ring transformation of 5‐amino‐1,3‐thiazoles to imidazole‐5‐thiols

NISPEN, S. P. J. M. VAN; Bregman, Jacob H.; Engen, D. G. Van; Leusen, A. M. Van; Saikachi, Haruo; Kitagawa, Toshiaki; Sasaki, Hideaki

doi:10.1002/recl.19821010102

Cited by 9 publications

(2 citation statements)

References 19 publications

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“…The injection temperature of 40 °C used in method 2b gave a good yield of erucin. This observation is supported by reports of isothiocyanates getting converted into thiazole and isothiazole at high temperature as reported by Van Nispen and others () and Mukerjee and Ashare ().…”

Section: Resultssupporting

confidence: 87%

Evaluating Extraction Conditions of Glucosinolate Hydrolytic Products from Seeds of Eruca sativa (Mill.) Thell. Using GC‐MS

Arora

Sharma

Kumar

et al. 2014

Journal of Food Science

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Glucosinolate hydrolytic products are important volatile metabolites that are difficult to extract. The different conditions, such as extraction method, solvent, and dryingmethods, are responsible for successful extractions. An improved extraction method will help in a better isolation of these valuable compounds, which may then be used for different biological activities such as anticancer, antimutagenic, bioherbicidal, antimicrobial, antigenotoxic, and antitumor activities.

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Section: Resultssupporting

confidence: 87%

Evaluating Extraction Conditions of Glucosinolate Hydrolytic Products from Seeds of Eruca sativa (Mill.) Thell. Using GC‐MS

Arora

Sharma

Kumar

et al. 2014

Journal of Food Science

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“…A literature search showed that 4-tosyl-1-arylimidazoles were already reported via different synthetic strategies. For example, they could be prepared by reacting arylazasulfones 5 with TosMIC or via oxidation of dilithiated 1-phenyl-4-tosyl-1 H -imidazole-5-thiol 6 with alkaline potassium ferricyanide or, finally, via reaction between aryl formamidate 7 or aryl formamidines and TosMIC in the presence of sodium hydride (Figure ).…”

mentioning

confidence: 99%

Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

et al. 2019

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Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism in two different ways, with the second molecule undergoing a novel type of fragmentation resulting in the incorporation of a C−H into the final product.

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Synthetic Uses of Tosylmethyl Isocyanide (TosMIC)

Leusen

2001

Organic Reactions

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TosMIC is the acronym for 4‐tolylsulfonylmethyl isocyanide or tosylmethyl isocyanide. It is the best‐known member of a series of about 25 sulfonyl‐substituted methyl isocyanides RSO 2 CH 2 NC collected in Chart 1 (p. 426). TosMIC is a multipurpose synthetic reagent. It is by far the most versatile synthon derived from methyl isocyanide. This chapter provides a complete account of the synthetic uses of TosMIC based on a literature search closed in January 1996, and supplemented with further data available to the authors. Also included are applications of some of the more important TosMIC homologs (TosCHRNC). TosMIC is the only commercially available sulfonylmethyl isocyanide. It is a stable, colorless, practically odorless solid, which can be stored at room temperature without decomposition. Four brief review papers on the chemistry of TosMIC have appeared, in 1980, 1987, 1993, and 1995. Several reviews on the chemistry of isocyanides in general are available. An effort has been made to make this chapter as complete as possible, in coverage both by tables and by references, with respect to the immediate objective: a survey of the “Synthetic Uses of TosMIC.” Emphasis is on the primary products derived from reactions of TosMIC and related isocyanides, with limited reference to the further utilization of these products. Thus, the next section gives a complete account of reductive cyanation, the conversion of aldehydes or ketones into cyanides with the use of TosMIC, but for obvious reasons synthetic applications of the product cyanides are not treated in this chapter. One of the subsequent sections describes the application of TosMIC to the synthesis of pyrroles, including 2,3‐divinylpyrroles, which are important precursors in a new synthesis of indoles. This latter transformation, made possible by the easy availability of the precursors through TosMIC chemistry, is afforded brief coverage. As a rule, reference to preliminary papers has been omitted when the same information is available from the corresponding full papers. The patent literature is covered highly selectively and is cited only when providing new and relevant information. Negative results of reactions are reported in the text or tables only when at least some relevant information is available with respect to the conditions of such unsuccessful attempts.

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Synthesis of thiazoles and imidazoles from isothiocyanates and tosylmethyl isocyanide. Base‐induced ring transformation of 5‐amino‐1,3‐thiazoles to imidazole‐5‐thiols

Cited by 9 publications

References 19 publications

Evaluating Extraction Conditions of Glucosinolate Hydrolytic Products from Seeds of Eruca sativa (Mill.) Thell. Using GC‐MS

Evaluating Extraction Conditions of Glucosinolate Hydrolytic Products from Seeds of Eruca sativa (Mill.) Thell. Using GC‐MS

Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

Synthetic Uses of Tosylmethyl Isocyanide (TosMIC)

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