Attempted synthesis of a keto diazene: reactions of propargylic amines, sulfamides, and ureas

Chiu, Sai Keung; Dube, Michael F.; Keifer, Leonard; Szilagyi, Sandor; Timberlake, Jack W.

doi:10.1021/jo00395a015

Cited by 16 publications

(4 citation statements)

References 8 publications

(16 reference statements)

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“…Imidazolidin-2-ones 891 were first prepared in 50−78% yields in 1978 by Timberlake and co-workers by treatment of propargylureas with NaH. 469 A more recent method of this transformation has been developed by Padwa who instead treated propargylurea 892 with AuCl 3 leading to imidazolidin-2-one 893 in a 68% yield. This latter isomerized to yield dihydroimidazol-2-one 894 following heating in toluene and in the presence of PTSA 383…”

Section: Synthesis Of Imidazoles From Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Section: Synthesis Of Imidazoles From Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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“…N- (1,acetamide 1a was prepared from acetic anhydride and acetylenic amine. 19 Benzamides 1b and 1d, acrylamide 1e, picolinamides 1g and 1h, terephthalic diamide 11i, 2,2-dimethylmalonamide 11j, and pyridine-2,6dicarboxylic acid (1,1-dimethylprop-2-ynyl) amide 11k were prepared causing the respective acid chloride to react with acetylenic amines according to the procedures reported in the literature. 20 late 1f and bis(1,1-dimethylprop-2-ynyl)-1,2-cyclohexyldicarboxamide 11l were obtained by transforming the corresponding carboxylic group into amide through reaction with N-hydroxysuccinimide and subsequently with acetylenic amine according to a procedure reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

“…N -(1,1-Dimethylprop-2-ynyl)acetamide 1a was prepared from acetic anhydride and acetylenic amine . Benzamides 1b and 1d , acrylamide 1e , picolinamides 1g and 1h , terephthalic diamide 11i , 2,2-dimethylmalonamide 11j , and pyridine-2,6-dicarboxylic acid (1,1-dimethylprop-2-ynyl) amide 11k were prepared causing the respective acid chloride to react with acetylenic amines according to the procedures reported in the literature .…”

Section: Methodsmentioning

confidence: 99%

Efficient and General Synthesis of 5-(Alkoxycarbonyl)methylene-3-oxazolines by Palladium-Catalyzed Oxidative Carbonylation of Prop-2-ynylamides

et al. 2002

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A variety of prop-2-ynylamides have been carbonylated under oxidative conditions to give oxazolines, oxazolines with chelating groups, and bisoxazolines bearing an (alkoxycarbonyl)methylene chain at the 5 position in good yields. The cyclization-alkoxycarbonylation process was carried out in alcoholic media at 50-70 degrees C and under 24 bar pressure of 3:1 carbon monoxide/air in the presence of catalytic amounts of 10% Pd/C or PdI2 in conjunction with KI. Cyclization occurred by anti attack of an oxygen function on the palladium-coordinated triple bond, followed by stereospecific alkoxycarbonylation, strictly resulting in E-stereochemistry. The structures of representative oxazolines and bisoxazolines have been determined by X-ray diffraction analysis.

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“…1-Methyl-and l-acetyl-3tert-butyl-5,5-dimethyl-2,4imidazolidinedione (lc and Id) were obtained in 86 and 60% yields from ozonolysis of the corresponding imidazolidinones 6c and 6d. 10 3-(JV-Phenylcarbamyl)-and 3-[(diethylamino)ethyl]-5.5-dimethyl-2,4-imidazolidinedione (le and lg) and 3-[(diethylamino)ethyl]-and l,3-bis[(diethylamino)ethyl]-5.5-diphenyl-2,4-imidazolidinedione (lh and li) were prepared in 66, 59, 61, and 40% yields, respectively, by treating the sodium salt of the dimethylor diphenylimidazolidinedione, formed from NaH in THF, with phenyl isocyanate or 5-chloroethyldiethylamine hydrochloride. 22 5,5-Dimethyl-3-(p-toluenesulfonyl)-2,4-imidazolidinedione (If).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of imidazolidinediones and oxazolidinediones from cyclization of propargylureas and propargyl carbamates

Chiu¹,

Keifer²,

Timberlake³

1979

J. Med. Chem.

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A synthetic procedure for the preparation of imidazolidinediones by the base-catalyzed cyclization of propargylureas is described. This method appears to be the most versatile way of obtaining these compounds containing tertiary groups substituted on ring-nitrogen number 3. One of these derivatives, 3-tert-butyl-5,5-dimethyl-2,4-imidazolidinedione (1a), has shown a moderate level of subcutaneous metrazole seizure threshold activity (scMet indicates potential for control of petit mal epileptic seizures) in control screens on mice, as determined by the National Institute of Neurological and Communicative Disorders and Stroke.

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Attempted synthesis of a keto diazene: reactions of propargylic amines, sulfamides, and ureas

Cited by 16 publications

References 8 publications

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Synthesis and Reactivity of Propargylamines in Organic Chemistry

Efficient and General Synthesis of 5-(Alkoxycarbonyl)methylene-3-oxazolines by Palladium-Catalyzed Oxidative Carbonylation of Prop-2-ynylamides

Synthesis of imidazolidinediones and oxazolidinediones from cyclization of propargylureas and propargyl carbamates

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