Reactions of Cycloalkanone Oxime <i>p</i>-Toluenesulfonates

Satô, Tadashi; Wakatsuka, H.

doi:10.1246/bcsj.42.1955

Cited by 6 publications

(2 citation statements)

References 4 publications

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“…(C13H19N04S) , N; C: caled, 54.72; found, 54.25. Diethyl lV- sulfonyl]methylamino]pentanoyl]-L-glutamate (8b). A stirred mixture of 8a (9.4 g, 33 mmol) and diethyl L-glutamate hydrochloride (7.9 g, 33 mmol) in CH2C12 (60 mL) was treated with N,N-dicyclohexylcarbodiimide (DCC; 3.4 g, 16 mmol) and Et3N (3.3 g, 33 mmol). Addition of another 3.4-g portion of DCC caused an exothermic reaction, and the mixture was cooled externally to 25 °C and then left overnight.…”

Section: -[[(4-methylphenyl)sulfonyl]methylamino]pentanoicmentioning

confidence: 99%

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Analogs of methotrexate

Piper¹,

Elliott²,

Temple³

et al. 1979

J. Med. Chem.

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Analogues of methotrexate (MTX) were prepared by alkylation of side-chain precursors with 6-(bromomethyl)-2,4-pteridinediamine followed, where necessary, by saponification of the intermediate esters and, in two cases, by electrophilic substitution reactions in the pyridine ring portion of 3-deazamethotrexate. Effects of the various modifications on their ability to inhibit dihydrofolate reductase, cytotoxicity, and activity against L1210 leukemia in mice were examined in light of recent findings concerning active transport of MTX and related compounds and the binding features of the MTX-dihydrofolate reductase complex.

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Section: -[[(4-methylphenyl)sulfonyl]methylamino]pentanoicmentioning

confidence: 99%

“…Removal of the phenyl group by an additional methylene group (38) restores enzyme inhibition to a large extent and results in some cytotoxicity but not L1210 activity. Minor changes in the benzene ring, such as chlorination (33) or substitution of the pyridine ring for it (34), are well tolerated, (1964)]. c The /50 for MTX varied from 0.014 to 0.045 µ .…”

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confidence: 99%

Analogs of methotrexate

Piper¹,

Elliott²,

Temple³

et al. 1979

J. Med. Chem.

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Meerwein's Catalytic Beckmann Rearrangement

et al. 1996

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Meerwein recommended nitrilium salts (2) as catalysts for the Beckmann rearrangement of oximes (1) under neutral and water‐free conditions. For the first time, primary adducts (Z)–(3) of oximes to nitrilium salts have been isolated. Reported are activation energies for Beckmann rearrangements of these adducts, and an X‐ray structural analysis of (Z)–3a. Rearrangement of 3 produces mixtures of up to four different N‐acylamidinium salts 5–8, which arise from fast reactions of primary‐formed secondary amides (4) with nitrilium salts (2). Because of their ambident electrophilic character the N‐acylamidinium salts react with excess of oxime not only to amides (4) but to mixtures of products. It is shown that nitrilium salts cannot be used as catalysts for the Beckmann rearrangement.

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