A Novel Route for Chiral Synthesis of the Triazole Antifungal ER-30346.

Kaku, Yumiko; Tsuruoka, Akihiko; Kakinuma, Hiroyuki; Tsukada, Itaru; Yanagisawa, Manabu; Naito, Toshiki

doi:10.1248/cpb.46.1125

Cited by 27 publications

(14 citation statements)

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“…Considering that 1,2,4-triazole scaffolds possess good biocompatibility and tissue bioactivity, [15] and are found in antimicrobial agents such as terconazole, fluconazole, and itraconazole, as well as in aromatase inhibitors anastrozole and letrozole, we explored the scope with respect to hydrazonyl chlorides. Gratifyingly, as depicted in Scheme 3, a series of aryl-and alkyl-substituted hydrazonyl chlorides were suitable for this conversion, affording 1,3,5-trisubstituted-1,2,4-triazoles in moderate to excellent yields.…”

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confidence: 99%

Deconstructive Oxygenation of Unstrained Cycloalkanamines

et al. 2020

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A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto‐oxidative aromatization promoted C(sp3)−C(sp3) bond cleavage strategy. This metal‐free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto‐oxidative annulation to in situ generate pre‐aromatics, followed by N‐radical‐promoted ring‐opening and further oxygenation by 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) and m‐cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4‐triazole‐containing acyclic carbonyl compounds were efficiently produced. This protocol features a one‐pot operation, mild reaction conditions, high regioselectivity and ring‐opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids.

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confidence: 99%

Deconstructive Oxygenation of Unstrained Cycloalkanamines

et al. 2020

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“…[2][3][4][5][6] In this context, M. Soukup from Hoffmann-La Roche developed also a new convergent synthesis of ravuconazole. [7] The key step of this synthesis is based on a chiral allene addition reaction catalyzed by palladium, where a zinc-allene derivative generated from a chiral propargylic mesylate is reacted with a benzophenone derivative (Scheme 1).…”

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confidence: 99%

Improved Chiral Synthesis of Ravuconazole

Muller

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et al. 2009

Synthetic Communications

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“…It has been noticed that triazol has different usages in research works as a building block for complex chemical compounds like pharmaceutical drugs such as the antibacterial, antifungal, antiviral, anticancer, antimicrobial, antidepressant, anticonvulsant, central nervous system modulators, and anti‐inflammatory ones . Several methods have been claimed for the synthesis of 1,2,3‐triazoles.…”

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confidence: 99%