Condensation of 1,2‐dithiols with α‐keto aldehydes. A Convenient synthesis of 2‐methyl‐1,3‐dithiolane‐2‐carboxaldehydes

Fridinger, T. L.; Henery-Logan, Kenneth R.

doi:10.1002/jhet.5570080318

Cited by 12 publications

(2 citation statements)

References 4 publications

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“…The equipment consisted of a doublepiston pump 6000 A (Waters, Eschborn, FRG), injector U6K (Waters), and a variable-wavelength detector 87.00 (Knauer, Bad Homburg, FRG) or a diode-array detector HP 1040 A with an HP 85 computer (Hewlett-Packard, Düsseldorf, FRG). Stainless (6) Grimmett, M. R. Ady. Heterocycl.Chem.…”

Section: Methodsmentioning

confidence: 99%

2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole: detection in commercial Caramel Color III and preparation by a model browning reaction

Kröplien¹,

ROSDORFER²,

Greef³

et al. 1985

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole: detection in commercial Caramel Color III and preparation by a model browning reaction

Kröplien¹,

ROSDORFER²,

Greef³

et al. 1985

J. Org. Chem.

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“…The acid-catalyzed condensation of a 1,2-or 1,3-dithiol with one equivalent of pyruvaldehyde or an -diketone afforded the desired carbonylsubstituted 1,3-dithiolane or 1,3-dithiane, respectively. The general novelty of the reaction plus the surprising specificity of dithiols toward pyruvaldehyde to afford exclusively the mercaptol aldehydes rather than the anticipated mercaptal ketones will be the subjects of a forthcoming publication (Fridinger and Henery-Logan, 1971). The open-chain compound 2,2-bis(methylthio)propionaldehyde was prepared by the acid-catalyzed condensation of acetaldehyde with methanethiol to afford acetaldehyde dimethyl mercaptal (Gibson, 1931), which was converted to its anion with butyllithium and then formylated with dimethylformamide (Corey and Seebach, 1965).…”

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confidence: 99%

Synthesis and biological activity of .alpha.-mercaptol O-(carbamoyl)oximes

Fridinger¹,

Mutsch²,

Matteson³

1971

J. Agric. Food Chem.

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The selective condensation of a-dicarbonyl comlane-2-carboxaldehyde 0-(methylcarbamoy1)oxime pounds with one equivalent of a dithiol followed by has exhibited especially outstanding greenhouse and oxime formation and subsequent carbamoylation field control of nematodes with no phytotoxicity. has afforded a series of novel a-mercaptol 0-Structure us. activity relationships appear to be (carbamoyl)oximes, some of which possess good consistent with previously studied cholinesteraseto excellent insecticidal, acaricidal, and nematicidal inhibiting carbamates. Toxicological aspects are activity. The compound 2,4-dimethyl-1,3-dithiodiscussed.he continuing search for improved carbamate insecticides has led, in the last decade, to a class of potent T acetylcholinesterase inhibitors derived from a variety of oxime precursors. For example, significant pesticidal activity has been reported for 0-(carbamoy1)oximes of cycloaliphatic and bicyclic ketones (Kilsheimer and Manning, 1963;Weiden, 1968), 2-keto-1,3-dithiolanes (Addor, 1965), 5-keto-l,3-dithianes (Addor, 1968), alkoxy and alkylthio esters (Felton, 1968), and trisubstituted acetaldehydes (Payne et al., 1966;Weiden, 1968). Detailed structure ES. activity studies of the latter class of compounds, exemplified by 2-methyl-2-(methylthio)propionaldehyde 0-(methylcarbamoy1)-oxime (aldicarb, Temik, UC 21149), have defined certain important criteria for high or optimum acetylcholinesterase inhibition. These include a conformational similarity to acetylcholine, the presence of an a-alkylthio (or electronegative) substituent, and monomethylation of the carbamate nitrogen. The special role of sulfide sulfur is also apparent in other 0-(methylcarbamoy1)oximes ; for example, Smethyl N-[(methylcarbamoyl)oxy]thioacetimidate (methomyl, Lannate, DuPont 1179), in substituted thiophenyl carbamates (Mahfouz ef a/., 1969), and in the case of certain (methylcarbamoy1oxy)benzaldehyde mercaptals (Durden and Weiden, 1969;Nikles, 1969). The present work describes a new series of insecticidalnematicidal a-mercaptol 0-(carbamoy1)oximes of general structure I. The compound 2,4-dimethyl-1,3-dithiolane-2-carboxaldehyde 0-(methylcarbamoy1)oxime (MBR 6168, Tirpate) has demonstrated especially outstanding greenhouse and field nematode control with no phytotoxicity, and is currently under development by 3M Company. 0 0 II RIS -C I -CR3 II R,S NOCNReRs ii CH 3 < ? \OCNHCH3

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ChemInform Abstract: KONDENSATION VON 1,2‐DITHIOLEN MIT ALPHA‐KETOALDEHYDEN, EINE BEQUEME SYNTHESE VON 2‐METHYL‐2‐FORMYL‐1,3‐DITHIOLANEN

Fridinger¹,

Henery-Logan²

1971

Chemischer Informationsdienst. Organische Chemie

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Condensation of 1,2‐dithiols with α‐keto aldehydes. A Convenient synthesis of 2‐methyl‐1,3‐dithiolane‐2‐carboxaldehydes

Cited by 12 publications

References 4 publications

2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole: detection in commercial Caramel Color III and preparation by a model browning reaction

2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole: detection in commercial Caramel Color III and preparation by a model browning reaction

Synthesis and biological activity of .alpha.-mercaptol O-(carbamoyl)oximes

ChemInform Abstract: KONDENSATION VON 1,2‐DITHIOLEN MIT ALPHA‐KETOALDEHYDEN, EINE BEQUEME SYNTHESE VON 2‐METHYL‐2‐FORMYL‐1,3‐DITHIOLANEN

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