Novel Variant of Recyclization of N-Arylmaleimides when Reacted with Aminoazoles

Kovygin, Yu. A.; Krylski, D. V.; Zorina, Anna V.; Shikhaliev, Kh. S.

doi:10.1023/b:cohc.0000048301.26073.e1

Cited by 5 publications

(11 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The H-NMR data for compound 4a, which was prepared similar to described in Ref. 6, were absolutely consistent with described values. Compounds 4 showed enhancement of the signal of triazole proton (at 8.33 ppm) by irradiation of the H X proton of ABX system (the signal at 5.30 ppm) in the NOE experiment (Scheme 5); compound 5 showed no such effect, which is consistent with structures of 4 and 5 given above.…”

Section: Resultssupporting

confidence: 84%

“…The single product (6) was isolated; its analytical data were consistent with given in [6]. According to NMR data including NOE experiments (Scheme 6), the structure of 6 was assigned as given on Scheme 4.…”

Section: Resultssupporting

confidence: 57%

“…6), in ethanol and n-penthanol, in acetic acid and by melting together without solvent by 150-160 C. As a result, compounds 4a-g and 5a-g were prepared (Scheme 4). It was established that when carrying out in dioxane or isopropanol reaction leads regioselectively to formation of compounds 4.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction of aminoazoles containing the amidine moiety, especially, 3-amino-1,2,4-triazole (1) and 2-aminobenzimidazole (2), with N-aryl derivatives of maleimides was firstly reported at [6], according to which the reaction leads to formation of azolopyrimidine derivatives 4 and 6; the structure assignment was made based exclusively on 1 H-NMR spectra in this case (Scheme 2). Our previous research showed that in the reactions of hererocyclic aminoazoles, like 1 and similar, with carbonyl bielectrophiles different isomeric products can be obtained.…”

Section: Introductionmentioning

confidence: 99%

“…7 and polyelectrophilic nature of compound 3, by establishing the structure of products described in Ref. 6 additional data are necessary to be involved.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Reactions of N‐arylmaleimides with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole

Rudenko

Komykhov

Мусатов

et al. 2011

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The reaction of 3‐amino‐1,2,4‐triazole (1) with N‐arylmaleimides leads to azolopyrimidines 4 and 5. The 2‐aminobenzimidazole (2) in the reaction with 3 gives the pyrimidobenzimidazoles 6. In similar conditions, the reaction of amine 2 with maleic anhydride (7) leads to formation of 2‐oxo‐1,2,3,4‐tetrahydropyrimido[1,2‐a]benzimidazole‐4‐carboxylic acid (8). The structures of 4, 5, 6, and 8 were proved by X‐Ray and NOE NMR measurements. J. Heterocyclic Chem., (2011)

show abstract

Section: Resultssupporting

confidence: 84%

Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…7 and polyelectrophilic nature of compound 3, by establishing the structure of products described in Ref. 6 additional data are necessary to be involved.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Reactions of N‐arylmaleimides with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole

Rudenko

Komykhov

Мусатов

et al. 2011

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

Novel Variant of Recyclization of N‐Arylmaleimides When Reacted with Aminoazoles.

et al. 2005

View full text Add to dashboard Cite

show abstract

Recyclization Reactions of N-Arylmaleimides with Polynucleophilic Compounds*

Zorina

Stolpovskaya

Shikhaliev

et al. 2015

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

The interaction of N-arylmaleimides with N-substituted biguanides and amidinothiourea gave new substituted imidazolinones and thiazolinones.Substituted imidazolinones and thiazolinones are known to possess a wide range of biological activity [1][2][3]. At the same time, the presence of several reactive functional groups in the structure offers opportunities for using these compounds as substrates in the synthesis of new heterocyclic compounds. On the other hand, N-arylmaleimides are frequently used for molecular design of various heterocyclic linearly linked and condensed matrices [4][5][6][7][8][9][10]. Previously it has been demonstrated that N-arylmaleimides react as C(3)-electrophiles with various 1,4-bisnucleophiles, resulting in the formation of six-membered heterocyclic systems: piperidinones [6], hydrogenated thiazinones [11][12], and oxazinones [13]. At the same time, arylmaleimides react with 1,3-bisnucleophiles less predictably and may serve as С(3)-electrophiles, forming five-membered heterocyclic systems: pyrrolidines [4,8], imidazolinones [7], thiazolinones [14-16], or serve as С(4)-electrophiles, leading to six-membered heterocycles, respectively [7-9, 17]. Mixtures of five-membered and sixmembered heterocyclic systems are often formed [7,9].The goal of this work was to study recyclization reactions of N-arylmaleimides in the presence of N,N-and N,S-polynucleophiles, such as N-substituted biguanides and amidinothiourea.Despite the fact that N-substituted biguanides 1а-c represent polynucleophilic compounds, cyclization with N-arylmaleimides involved the guanidine fragment. The reactions were performed by refluxing the starting materials in methanol for 5-7 h. Apparently, the first step involved addition of the amino group in terminal guanidine fragment of bisguanide to arylmaleimide double bond [18], while in the second step the succinimide fragment was attacked by the nucleophilic nitrogen atom of imino group, resulting in recyclization with the formation of imidazolinone ring. This reaction was used for the synthesis of a range of substituted N-aryl-(4-oxo-4,5-dihydro-1Н-imidazol-5-yl)acetamides 2а-e. The use of dioxane or DMF as solvent decreased the yields of target products due to the occurrence of many side reactions.

show abstract

Novel Variant of Recyclization of N-Arylmaleimides when Reacted with Aminoazoles

Cited by 5 publications

References 2 publications

Reactions of N‐arylmaleimides with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole

Reactions of N‐arylmaleimides with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole

Novel Variant of Recyclization of N‐Arylmaleimides When Reacted with Aminoazoles.

Recyclization Reactions of N-Arylmaleimides with Polynucleophilic Compounds*

Contact Info

Product

Resources

About