Nitrosochlorination reaction of substituted imidazolin-2-ones

Golovko, V. V.; Statsenskaya, A. I.; Baskakov, Yu. A.; Putsykin, Yu. G.

doi:10.1007/bf00473483

Cited by 3 publications

(7 citation statements)

References 2 publications

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“…In the first case, protective benzyl group was removed in the presence of Pd/C, followed by hydrolysis in the presence of HCl accompanied by heterocyclization with simultaneous decarboxylation, leading to imidazolone 1f in quantitative 2) 8 N NaOH 3 3 yield. 35 In the second case, the reaction was performed in MeCN with subsequent hydrolysis in aqueous methanol solution of HCl, 31 and the yield of compound 1g in this reaction reached 90%. No ureidoacetal intermediates were isolated in either of the cases.…”

Section: Scheme 10mentioning

confidence: 99%

“…27,28 The reaction conditions ranged from room temperature [25][26][27][28][29][30] to reflux 31 or cooling, 27,28 and the duration was from 30 min to 3 days. The second stage of the process involved acid-catalyzed cyclization of the synthesized ureidoacetals 6 with the formation of imidazolones 1 in the presence of HCl, 25,27,28,30,31 TFA, 26,29 AcOH, 32 and HCO 2 H. 33 We should note that compounds 6 in some cases were not isolated, with both stages performed as a one-pot process.…”

Section: Synthesis Of Imidazolones By Reaction Ofmentioning

confidence: 99%

“…HCl (Scheme 22). 31 Compounds 8 were synthesized from 2-amino-1-phenylethanone 18a and the corresponding isocyanates 10 in the presence of triethylamine. The yields of imidazolones 1 after recrystallization from EtOH reached 72-95%.…”

Section: Synthesis Of Imidazolones Based On Ureidoketonesmentioning

confidence: 99%

“…Ureidoacetals 6 may be obtained by interaction of α-aminоacetals 9 with isocyanates 10 (method I) 25 The obtained ureidoacetals 6 underwent cyclization to the imidazolone 1 in the presence of various acids, including hydrochloric, 1,25,27,28,30,31,[34][35][36][40][41][42][43][44]47 trifluoroacetic, 26,29 acetic, 32,48 formic, 33,37,45 and sulfuric acid 38,39 (Scheme 4).…”

Section: Synthesis Of Imidazolones From Ureidoacetalsmentioning

confidence: 99%

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Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Antonova

Баранов

Кравченко

2015

Chem Heterocycl Comp

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Section: Scheme 10mentioning

confidence: 99%

Section: Synthesis Of Imidazolones By Reaction Ofmentioning

confidence: 99%

Section: Synthesis Of Imidazolones Based On Ureidoketonesmentioning

confidence: 99%

Section: Synthesis Of Imidazolones From Ureidoacetalsmentioning

confidence: 99%

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Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Antonova

Баранов

Кравченко

2015

Chem Heterocycl Comp

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“…In many cases such synthesis is accompanied by other transformations. Thus, the reactions of 1,5-diarylimidazolin-2-ones 98 with nitrosyl in alcohols lead to 5-alkoxy-4-hydroxyiminoimidazolidin-2-ones 99 with yields of 73-85% [98]. In the NaNO 2 /AcOH system the imidazo[1,2-a]benzimidazole 100 gives the nitroso derivative 101, the treatment of which with an alcohol solution of alkali leads to the oxime 102 with a yield of 47% [99].…”

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confidence: 99%

Oximes of five-membered heterocyclic compounds with two heteroatoms. 1. Synthesis and structure (Review)

Абеле

Lukevics

2007

Chem Heterocycl Compd

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Data on the production and structure of oxazole, thiazole, and imidazole aldoximes, ketoximes, and amidoximes and their derivatives are reviewed.The oximes of five-membered heterocyclic compounds with two heteroatoms are widely used as intermediates in fine organic synthesis. The principal methods for the production of oxazole, thiazole, and imidazole aldoximes, ketoximes, amidoximes, and their derivatives are summarized in this review. The principal methods of investigation of the structure of the oximes of five-membered heterocyclic compounds with two heteroatoms in relation to their isomerism are examined briefly. The characteristics of the reactions and biological activity of the oximes of five-membered heterocyclic compounds with two heteroatoms will be presented in the second part of the review.

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Synthesis of Symmetrically and Unsymmetrically Substituted N,N′-Diarylimidazolin-2-ones by Copper-Catalyzed Arylamidation under Microwave-Assisted and Conventional Conditions

Hafner¹,

Kunz²

2007

Synthesis

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A convenient synthesis of unsymmetrically substituted N,N¢-diarylimidazolin-2-ones is reported. Starting from 2,2-dimethoxyethylamine, the first aryl group was introduced by reaction with arylisocyanate and subsequent cyclization to afford Narylimidazolin-2-ones. The second arylation step was then accomplished by microwave-assisted copper-catalyzed arylamidation of the N-arylimidazolin-2-ones with a variety of aryliodides and arylbromides to give unsymmetrically substituted N,N¢-diarylimidazolin-2-ones. Symmetrically substituted N,N¢-diarylimidazolin-2-ones could also be prepared from imidazolin-2-one in a two-fold copper-catalyzed arylamidation, however, the nature of the substrate limits the use of this reaction.A convenient and straightforward approach to the synthesis of a library of unsymmetrically substituted N,N¢-diarylimidazolin-2-ones has not yet been developed, even though this class of compounds exhibits interesting biological activities 1 and is used in a number of electrophotographic processes. 2 The standard method with which to prepare symmetrically and unsymmetrically diarylsubstituted imidazolin-2-ones is based on the preparation of the respective N,N¢-diaryl-substituted urea acetal C by condensation of 1-(N-arylamino)ethylacetal A with arylisocyanate B, followed by cyclization to the N,N¢-diarylimidazolin-2-one D (Scheme 1). 3

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Nitrosochlorination reaction of substituted imidazolin-2-ones

Cited by 3 publications

References 2 publications

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Oximes of five-membered heterocyclic compounds with two heteroatoms. 1. Synthesis and structure (Review)

Synthesis of Symmetrically and Unsymmetrically Substituted N,N′-Diarylimidazolin-2-ones by Copper-Catalyzed Arylamidation under Microwave-Assisted and Conventional Conditions

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Nitrosochlorination reaction of substituted imidazolin-2-ones

Cited by 3 publications

References 2 publications

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Oximes of five-membered heterocyclic compounds with two heteroatoms. 1. Synthesis and structure (Review)

Synthesis of Symmetrically and Unsymmetrically Substituted N,N′-Diaryl­imidazolin-2-ones by Copper-Catalyzed Arylamidation under Microwave-Assisted­ and Conventional Conditions

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Synthesis of Symmetrically and Unsymmetrically Substituted N,N′-Diarylimidazolin-2-ones by Copper-Catalyzed Arylamidation under Microwave-Assisted and Conventional Conditions