Heterocyclization reactions of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones with ?-oxoketeneaminals

Гейн, В. Л.; Pitirimova, S. G.; Vinokurova, O. V.; Andreichikov, Yu. S.; Komkov, A. V.; Bogdanov, V. S.; Dorokhov, V. A.

doi:10.1007/bf00703703

Cited by 7 publications

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“…It was found earlier that compounds of this type are able to react with aroylketens, forming 4 pyrimidinone derivatives [5]. Trichloromethyl pyrim idines were obtained in [6] by the cyclocondensation reaction of esters of 2 (diaminomethylidene) 3 oxobutyric acid with trichloroacetonitrile ( Fig.…”

Section: Introductionmentioning

confidence: 99%

The role of intramolecular hydrogen bonds in nucleophilic addition reactions of ketenaminals

Isaev

2012

Russ. J. Phys. Chem.

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Section: Introductionmentioning

confidence: 99%

The role of intramolecular hydrogen bonds in nucleophilic addition reactions of ketenaminals

Isaev

2012

Russ. J. Phys. Chem.

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“…In this regard, of particular interest are the pyrimidine derivatives bearing alkyl substituents with several electron withdrawing groups (e.g., carbonyl and nitrile) in position “2” of the cycle. Thus, the well‐known method for preparing such compounds is cyclization of diaminomethylidene derivatives of diben‐zoylmethane or acetoacetic ester by aroylketenes .…”

Section: Introductionmentioning

confidence: 99%

Reaction of 6‐Methyl‐2‐Thiouracil and 6‐Phenyl‐2‐Thiouracil with Chloro‐β‐Dicarbonyl and Bromo‐β‐Dicarbonyl Compounds and Their Nitrile Analogs

Yavolovskii

Ivanov

Fonarı

et al. 2015

Journal of Heterocyclic Chem

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Derivatives of 2‐methylidene‐1,3‐dihydropyrimidin‐4‐ones 2a, 2b, 2c, 2d, 2e, 2f, 2g were synthesized by interaction of 6‐methyl‐2‐thiouracil and 6‐phenyl‐2‐thiouracil 1a, 1b with some activated halogenides: diethyl bromomalonate, ethyl 2‐chloro‐3‐oxobutanoate, ethyl 2‐bromocyanoacetate, 2‐bromo‐5,5‐dimethylcyclohexan‐1,3‐dione, and bromomalononitrile. The boiling of 1a with ethyl 2‐bromocyanoacetate in mixture of ethanol and EtONa results in intramolecular cyclization and formation of thiazolo[3,2‐a]pyrimidin‐5‐one 3. Interaction of 1a with 3‐chloropentane‐2,4‐dione and 2‐bromo‐1,3‐diphenylpropane‐1,3‐dione yielded corresponding S‐substituted thiopyrimidines 4a,4b. In general, the products of 1b S‐alkylation are less prone to sulfur extrusion. Reaction of 1b with diethyl bromomalonate in the absence of EtONa stops at the S‐alkylation step, while in the presence of EtONa in ethanol or PPh3 in dioxane 2‐(ethoxycarbonylmethyl)thio‐6‐phenyl‐1,3‐dihydropyrimidin‐4(1H)‐one 6 is formed exclusively. Molecular structure and crystal structure of 2‐(1,1‐diethoxycarbonylmethyliden)‐6‐methyl‐1,3‐dihydropyrimidin‐4(1H)‐one 2a are discussed.

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“…Earlier it has been found that compounds of this kind can react with aroylketenes to produce 4 pyrimidinone derivatives. 15 Herein, we report on cyclocondensation of alkyl 2 (diaminomethylidene) 3 oxobutyrates with trichloroacetonitrile.…”

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Synthesis of trichloromethylpyrimidines and trichloromethylpyrimido [4,5-d]pyrimidines from alkyl 2-(diaminomethylidene)-3-oxobutyrates and trichloroacetonitrile

2009

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Heterocyclization reactions of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones with ?-oxoketeneaminals

Cited by 7 publications

References 0 publications

The role of intramolecular hydrogen bonds in nucleophilic addition reactions of ketenaminals

The role of intramolecular hydrogen bonds in nucleophilic addition reactions of ketenaminals

Reaction of 6‐Methyl‐2‐Thiouracil and 6‐Phenyl‐2‐Thiouracil with Chloro‐β‐Dicarbonyl and Bromo‐β‐Dicarbonyl Compounds and Their Nitrile Analogs

Synthesis of trichloromethylpyrimidines and trichloromethylpyrimido [4,5-d]pyrimidines from alkyl 2-(diaminomethylidene)-3-oxobutyrates and trichloroacetonitrile

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