Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control

̆tlík, Jan Sve; Veizerová, Lucia; Kettmann, V.

doi:10.1016/j.tetlet.2008.03.136

Cited by 33 publications

(18 citation statements)

References 23 publications

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“…1 We reported a similar formation of oxygen-bridged pyrimidine 2 for the classical Biginelli condensation under standard conditions. The presence of two neighbouring ester groups in compounds 1, provides an opportunity for the elaboration of a further nitrogen heterocycle, fused onto the pyrimidine ring, without altering the parent bridged system.…”

Section: Introductionmentioning

confidence: 66%

“…In all correlation methods, gradient-enhanced versions of experiments were used to achieve superior suppression of unwanted coherence transfer pathways. 1 …”

Section: Methodsmentioning

confidence: 99%

“…This hydrazine reagent which has only one condensable nitrogen would presumably force the formation of a 6-6 fused system. Unfortunately, the desired cyclocondensation failed and we were able to isolate only a ring-open dihydropyrimidine 1,8 with a free phenolic moiety 8. The same product 8 was also obtained in the reaction of 1a with benzylamine as a result of transesterification and breaking of the oxygen-bridge.…”

Section: Esi-ms Showed An [M+h]mentioning

confidence: 99%

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Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Svêtlík¹,

Veizerová²,

Liptaj³

et al. 2009

Arkivoc

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The reactivity of oxygen-bridged Biginelli pyrimidines, such as 2,6-methano-1,3,5-benzoxadiazocines, towards nitrogen nucleophiles such as hydrazine hydrate, N,Ndimethylhydrazine, and benzylamine was studied. While all these reagents caused opening of the oxygen-containing ring, only the reaction with hydrazine furnished the corresponding pyrazolopyrimidine and pyridopyrimidine condensation products.1 H-15 N HMBC correlation spectroscopy was used for structure confirmation.

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Section: Introductionmentioning

confidence: 66%

“…In all correlation methods, gradient-enhanced versions of experiments were used to achieve superior suppression of unwanted coherence transfer pathways. 1 …”

Section: Methodsmentioning

confidence: 99%

Section: Esi-ms Showed An [M+h]mentioning

confidence: 99%

See 1 more Smart Citation

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Svêtlík¹,

Veizerová²,

Liptaj³

et al. 2009

Arkivoc

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“…Thus, the three- However, Sakhno et al The article [78] On the other hand, refluxing pyrazole 42, phenylpyruvic acid (15), and aromatic alde- i.e. oxygen-bridged [82][83][84][85][86][87][88], spiroheterocyclic compounds [89], lactones [85] and the other structures [82]. In continuation of the recent research [44,45,52,58,[78][79][80] min) or heating them in DMSO for 48 hours also caused the formation of heteroaromatic carboxylic acids 58 (Scheme 28) [90].…”

Section: General Partmentioning

confidence: 99%

Heterocyclization Reactions of Pyruvic Acids and Aminoazoles with Controlled Chemoselectivity

et al. 2015

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The present review includes the analysis of known literature data concerning linear and multicomponent heterocyclizations involving pyruvic acids and aminoazoles. In particular, the review demonstrates the approaches to control regio-and chemoselectivity of these types of treatments and their application to solve the matters of Diversity Oriented Synthesis. ________________________________________________________________________________ IntroductionThe significance of pyruvic acid in our life can be hardly overestimated. It plays a vital role as one of the most reactive substances among those of important in cellular metabolism. That is why a conclusion may be made that reactions involving pyruvic acid may help to solve some health problems and assist in finding a cure against various diseases today and in future. However, in this case no clear relationship between the electronic character of the substituents and structure of the reaction products was established.An interesting approach to the synthesis of quinoxaline derivatives via Ugi-type reaction was proposed as well (Scheme 3) [28]. Thus, the four-component reaction of the starting reagents in MeOH yielded the Ugi adducts, which by means of acid catalysis turned into quinoxalinones. Thus, the behavior of 3-amino-1,2,4-triazole (6) in the three-component condensation with aromatic aldehydes 2 and pyruvic acid (1) turned up to be quite the same to the 5-aminotetrazole (4) reactivity [45]. Refluxing 3-amino-1,2,4-triazole (6) and aromatic aldehydes 2 with pyruvic acid (1) in glacial acetic acid allowed to isolate from the reaction mixtures the pure acids 8 with good yields (Pathway B, Scheme 10). At the same time, heating the starting compounds 1, 2 and 6 in DMF led to mixtures of two regioisomeric dihydrotriazolopyrimidines 8 and 9 (Pathway D, Scheme 10). All attempts to separate these mixtures by crystallization or using HPLC were unsuccessful [45, 53].

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“…This has led to the development of several new synthetic strategies involving combinations of Lewis acids and transition metal salts, e.g. Sr(OTf) 2 [10], p-TsOH [11,12], HPA [13], NiCl2.6H2O [14], LaCl 3 [15], InBr 3 [16] and Bakers' yeast [17]. Obviously, most of these catalysts and solvents are not acceptable in the context of green synthesis.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐free synthesis of monastrol derivatives catalyzed by NaHSO₄

Cheng

Wang

et al. 2010

Journal of Heterocyclic Chem

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Monastrol derivatives were synthesized by environment-friendly three component condensation reaction of salicylaldehyde analogues, b-ketoester, and urea or thiourea under solvent-free conditions with NaHSO 4 as catalyst in high yields. The reactions formed two different monastrol products, 4-(2-hydroxyphenyl)pyrimidines 4 and 9-methyl-11-oxo(or thioxo)-8-oxa-10,12-diazatricyclotrideca derivatives 5.

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Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control

Cited by 33 publications

References 23 publications

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Heterocyclization Reactions of Pyruvic Acids and Aminoazoles with Controlled Chemoselectivity

Solvent‐free synthesis of monastrol derivatives catalyzed by NaHSO₄

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Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control

Cited by 33 publications

References 23 publications

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Transformation of oxygen-bridged pyrimidines with nitrogen nucleophiles and characterization of resulting products

Heterocyclization Reactions of Pyruvic Acids and Aminoazoles with Controlled Chemoselectivity

Solvent‐free synthesis of monastrol derivatives catalyzed by NaHSO4

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Solvent‐free synthesis of monastrol derivatives catalyzed by NaHSO₄