Synthesis and Bleaching Activity of 1,5-Disubstituted Imidazoles

Yamada, Naotaka; Kuwano, Eiichi; Kikuchi, Masamichi; Etō, Morifusa

doi:10.1271/bbb.56.1943

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…In 1992, Yamada et al [24e] . used 4‐benzyloxyacetophenone, and after bromination and condensation with formamide, imidazole was obtained in 4 % yield.…”

Section: Condensation Reactionsmentioning

confidence: 99%

Molecular Construction Using Formamide as a C1 Feedstock

Sacchelli,

Rocha,

Fantinel

et al. 2024

Eur J Org Chem

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Formamide (HCONH2), a well‐known organic compound in chemistry and biology, can be employed for molecular construction. The chemistry of formamide, which involves condensation reactions, transamidation reactions, cross‐coupling reactions, and radical reactions, can be explored to synthesize more complex organic compounds. The focus of this review is to discuss the widespread use of formamide as a relevant C‐1 building block in organic synthesis.

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“…In 1992, Yamada et al [24e] . used 4‐benzyloxyacetophenone, and after bromination and condensation with formamide, imidazole was obtained in 4 % yield.…”

Section: Condensation Reactionsmentioning

confidence: 99%

Molecular Construction Using Formamide as a C1 Feedstock

Sacchelli,

Rocha,

Fantinel

et al. 2024

Eur J Org Chem

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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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Bleaching Activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles

Yamada

Kusano

Kuwano

2002

Bioscience, Biotechnology, and Biochemistry

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A variety of 4-aryl-and 4-alkyl-3-(substituted benzylthio)-4H-1,2,4-triazoles were prepared and evaluated for their bleaching activity by the lettuce seedling test. Among the series of tested compounds, 4-(3-‰uoro-phenyl)-3-(4-tri‰uoromethylbenzylthio)-4H-1,2,4-triazole (39) exhibited the highest bleaching activity, causing complete bleaching symptoms at 10 mM. In the dark condition, compound 39 inhibited the formation of such carotenoids as b-carotene, violaxanthin, neoxanthin and lutein, resulting in the formation of z-carotene, phytoene, phyto‰uene and b-zeacarotene, which were not detected in the untreated control. Treatment by compound 39 at 50 mM resulted in the amount of accumulated z-carotene being seven-fold higher than that of phytoene, phyto‰uene and b-zeacarotene. These results suggest that compound 39 might have interfered with desaturation, especially z-carotene desaturation, during carotenoid biosynthesis.

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Synthesis and Bleaching Activity of 1,5-Disubstituted Imidazoles

Cited by 3 publications

References 6 publications

Molecular Construction Using Formamide as a C1 Feedstock

Molecular Construction Using Formamide as a C1 Feedstock

Synthetic Uses of Tosylmethyl Isocyanide (TosMIC)

Bleaching Activity of 4-Phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles

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