Über Thioacylisocyanate, IX. Reaktion mit Nitrosobenzol, Diazoalkanen und Nitronen zu 5‐gliedrigen Ringen

Goerdeler, Joachim; Schimpf, R.

doi:10.1002/cber.19731060515

Cited by 24 publications

(6 citation statements)

References 9 publications

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“…As evident from Table 1, the addition of 5% water to the reaction mixture leads to a marked increase in the reaction time and significant reduction in the preparative yield of the product of ring opening (5). In addition, the observed reaction times in the DMSO-H 2 O mixture did not correlate with the series of nucleophile basicities in either water or in DMSO (Table 1).…”

mentioning

confidence: 56%

“…In addition, 1,2,4-oxadiazol-5-ones are of interest as biologically active compounds [2]. The thermolysis [3,4] and basic hydrolysis [5,6] of oxadiazolones can give N'-substituted amidines which, in turn, are used as starting materials in the synthesis of heterocycles [7,8] and ligands [9,10] as well as in medicine, e.g. as inhibitors of cytomegalovirus DNA polymerase [11].…”

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confidence: 99%

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Synthesis of N'-substituted amidines through the cleavage an oxadiazolone heterocycle by weakly basic nucleophiles. Effect of the nature of the nucleophile and of the nucleophile/substrate molar ratio

Polienko

Grigor’yev

Voinov

2009

Chem Heterocycl Comp

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NaNO 2 has been studied. It was shown for the first time that, as in the case of NaOH and MeONa, the reaction occurs with opening of the oxadiazolone ring to form exo-N-substituted amidines. It was shown that the weakly basic nucleophiles readily react with substrates which contain a substituent sensitive to attack by such nucleophiles as NaOH or MeONa. The effect of the nature of the nucleophiles on the reaction course for opening of the oxadiazolone ring was also studied. It was found that the reactivity of the nucleophiles in DMSO changes in the series F -> CN -> N 3 ->NO 2 -> Cl -> Br -and qualitatively correlates with their basicities in this solvent. Examination of the effect of the ratio of the reagents on the degree of conversion of the starting oxadiazolone has shown that a quantity of nucleophiles less than one equivalent also allowed the cleavage reaction of the oxadiazolone heterocycle to go to completion through just increasing the reaction time. The experimental data obtained lends support to the proposed reaction scheme.The 1,3-dipolar cycloaddition reaction of isocyanates to aldonitrones is one of the most efficient methods of synthesizing heterocyclic compounds. The cycloadducts formed (1,2,4-oxadiazol-5-one derivatives) are characterized by high stability and are used to capture unstable nitrones in order to identify them in an _______ * Dedicated to Academician B. A. Trofimov in his 70 th jubilee.

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confidence: 56%

mentioning

confidence: 99%

Synthesis of N'-substituted amidines through the cleavage an oxadiazolone heterocycle by weakly basic nucleophiles. Effect of the nature of the nucleophile and of the nucleophile/substrate molar ratio

Polienko

Grigor’yev

Voinov

2009

Chem Heterocycl Comp

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“…In the reaction with nitrosobenzene 1,2,4-thiadiazolone 78 is formed [16]. The thermolysis of the diones 1 in the presence of diazoalkanes leads to derivatives of 4-thiazolone 79 [16]. In the case of phenylthiazolinedione 1 and diazoacenaphthene the spiro compound 80 is formed [35].…”

Section: Other Reactionsmentioning

confidence: 97%

“…It is interesting that diazoacetophenone plays the role of C-nucleophile during the reaction with the isocyanate 2 (Ar = Ph) and reacts with the formation of compound 35 [16]. In this reaction 2,3-dihydro-1,4-dioxin only forms the C-addition product 42, while 1-ethoxy-2-methylethylene forms the [4+2] cycloaddition product 43 [18].…”

Section: Thermolysis In the Presence Of C-nucleophilesmentioning

confidence: 98%

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Synthesis and chemical characteristics of 2-substituted thiazoline-4,5-diones. (Review)

Nekrasov

Obukhova

2006

Chem Heterocycl Compd

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Heterocycles from Hydroxylamines and Hydroxamic Acids

Katkevičs¹,

Kukosha²,

Lukevics³

2010

Patai's Chemistry of Functional Groups

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Hydroxylamines and hydroxamic acids are polyfunctional organic molecules and several reactive intermediates can be generated from them, therefore they have found broad application in the synthesis of various nitrogen and oxygen containing heterocycles by means of nulceophilic substitution or addition, electrophilic intramolecular aromatic substitution, as well as [2+4] and [3+2] cycloaddition reactions. This chapter surveys synthesis of heterocycles from the title compounds highlighting some distinguished reaction mechanism aspects, regio‐ and stereo selectivity issues and experimental details. It is arranged according to the size and type of heterocycles that allows fast but also explanatory insight into synthesis of the particular cycles.

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Über Thioacylisocyanate, IX. Reaktion mit Nitrosobenzol, Diazoalkanen und Nitronen zu 5‐gliedrigen Ringen

Cited by 24 publications

References 9 publications

Synthesis of N'-substituted amidines through the cleavage an oxadiazolone heterocycle by weakly basic nucleophiles. Effect of the nature of the nucleophile and of the nucleophile/substrate molar ratio

Synthesis of N'-substituted amidines through the cleavage an oxadiazolone heterocycle by weakly basic nucleophiles. Effect of the nature of the nucleophile and of the nucleophile/substrate molar ratio

Synthesis and chemical characteristics of 2-substituted thiazoline-4,5-diones. (Review)

Heterocycles from Hydroxylamines and Hydroxamic Acids

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