Spectroscopic Study of the Conformation of 2-Anilino-2-ethoxy-3-oxothiobutyric Acid Anilides

Zaleska, Barbara; Socha, Robert P.; Ciechanowicz-Rutkowska, M.; Pilati, T.

doi:10.1007/s007060070022

Cited by 6 publications

(11 citation statements)

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“…Methylpyridin-2-yl)-2-(phenylamino)-2-(phenylimino) 13 C NMR (CDCl 3 ): d = 161. 5,151.2,150.5,148.6,146.7,141.1,137.3,128.6,128.6,125.1,123.8,123.4,122.0,115.0,22.1 (CH 3 Anal. Calcd for C 20 H 18 N 4 O: C, 72.71; H, 5.49;N,16.96.…”

Section: N-(5-methylpyridin-2-yl)-3-oxobutanamide (4c)mentioning

confidence: 99%

“…13 C NMR (DMSO-d 6 ): d = 157.4 (CONH), 148.2, 147. 5,146.3,143.1,138.9,137.5,135.1,129.7,128.7,128.1,122.9,120.9,118.4,114.5,112.6,104.0,17.2 (CH 3 ). Anal.…”

Section: N-(pyridin-2-yl)-34-dihydroquinazoline-2-carboxamide (9a)mentioning

confidence: 99%

“…4a,b,d,5 Over the past few years, they have reported on the syntheses of various heterocyclic rings of 1,3-and 1,4-diazines 4 from thioanilides 1, whereas anilides 2 turned out to be unreactive. 5 In an attempt to modify the reactivity of 1, we decided to introduce pyridin-2-yls instead of aryl substituents in the amide moieties of 1, along with replacing the sulfur atom with an oxygen atom, in order to obtain pyridilides 3 ( Figure 1).…”

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confidence: 99%

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New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

Trzewik¹,

Cież²,

Hodorowicz³

et al. 2008

Synthesis

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New, stable a-amido-a-aminonitrones were obtained in good yields from 3-oxobutyric acid N-pyridin-2-ylamides and nitrosobenzene. The a-amido-a-aminonitrones were then used as new, versatile building blocks to obtaining various heterocycles with both bielectrophilic and binucleophilic reagents. With diiodomethane as reagent, 1,2,5-oxadiazine derivatives were formed, whereas reactions with aromatic 1,2-, 1,3-and 1,4-diamines yielded quinoxaline, quinazoline, perimidine, and dibenzo[d,f][1,3]diazepine derivatives, respectively.

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Section: N-(5-methylpyridin-2-yl)-3-oxobutanamide (4c)mentioning

confidence: 99%

“…13 C NMR (DMSO-d 6 ): d = 157.4 (CONH), 148.2, 147. 5,146.3,143.1,138.9,137.5,135.1,129.7,128.7,128.1,122.9,120.9,118.4,114.5,112.6,104.0,17.2 (CH 3 ). Anal.…”

Section: N-(pyridin-2-yl)-34-dihydroquinazoline-2-carboxamide (9a)mentioning

confidence: 99%

mentioning

confidence: 99%

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New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

Trzewik¹,

Cież²,

Hodorowicz³

et al. 2008

Synthesis

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“…Spectral data for compounds 1a-c and 3a are described in our previous work. 11 Yields are given for pure products.…”

Section: Figurementioning

confidence: 99%

“…Recently, we have reported 9,10 the synthesis of 1,3-and 1,4-diazines which used the C-2 disubstituted thioanilides of 3-oxobutanoic acid 1 (X = S) 11 in heterocyclization reactions with various diamines. We have found that good leaving groups at C-2 of compound 1 offer an entry to formation of six-and seven-membered rings by treatment with binucleophiles.…”

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confidence: 99%

A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Zaleska¹,

Trzewik²,

Grochowski³

et al. 2003

Synthesis

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New convenient methods for the synthesis of 1,2,3-thiadiazole, 1,3,4-thiadiazine, and 1,2,5-triazepine derivatives are reported. In the heterocyclization process, the reactivity of 1-thia-4-aza-1,3-butadiene system of syn-2-phenylhydrazono-3-oxothiobutanoic acid anilides was exploited.The structure and chemistry of the 1,2,3-thiadiazole system have been under active investigation for years. 1-3 Its derivatives are useful in the treatment of hyperproliferative disorders including tumor growth and angiogenesis, and lymphoproliferative symptoms. 4 Moreover, derivatives of this system are applied in the treatment and/or prevention of morbid states mediated by oxytocin, including premature labour and dysmenorhea. 5 The 1,2,3-thiadiazole moiety is crucial for the antibacterial activity of new carbapenems 6 as well as for the efficacy of some pesticides. 7 The biological activity of 1,2,5-triazepines 8 has received less attention than the corresponding benzofused system.Recently, we have reported 9,10 the synthesis of 1,3-and 1,4-diazines which used the C-2 disubstituted thioanilides of 3-oxobutanoic acid 1 (X = S) 11 in heterocyclization reactions with various diamines. We have found that good leaving groups at C-2 of compound 1 offer an entry to formation of six-and seven-membered rings by treatment with binucleophiles. The reaction includes the initial nucleophilic attack of the nitrogen atoms of aliphatic 1,3-or 1,4-diamines on C-2 of compounds 1, followed by a novel sigmatropic rearrangement. On the other hand, the reactions of 1 with aliphatic 1,2-diamines lead to 1,4-diazines by ring expansion of the intermediate 1, 3-diazines. 12 In order to develop synthetic applications of thioanilides 1a-c in closing heterocyclic rings we have transformed them into phenylhydrazones 2a-c by treatment with phenylhydrazine (Scheme 1). The nucleophilic attack of the amino group of phenylhydrazine took place exclusively on the C-2 position of 2-anilino-2-methoxy-3-oxothiobutanoic acid anilides 1a-c.In contrast, the reaction of 2-anilino-2-methoxy-3-oxobutanoic acid anilide 3a (X = O), under similar conditions, exclusively provided osazone 4a (Scheme 1).Compounds 2a-c can appear in two isomeric forms corresponding to Z or E configuration of the 1-thia-4-aza-1,3-butadiene system. In solution, spectral data confirm the structure of the molecules of 2a-c as shown in Scheme 1 as the unique reaction product. X-ray analysis of 2a was carried out to prove the configuration in the solid state and precisely determine the molecular geometry. 14 A perspective view of molecule of 2a with the crystallographic atom numbering is presented in Figure 1. The central framework of the molecule, consisting of heteroatoms (S1, O1, N1-N3) and carbon atoms C1-C4, is quite flat. None of these atoms deviates from the least-squares plane passing through the heteroatoms by more than 0.1 Scheme 1Downloaded by: Chinese University of Hong Kong. Copyrighted material.

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Synthesis of Heterocyclic Systems by the Reaction of Zwitterionic Compounds with Isocyanates and Thiophosgene.

Zaleska

Karelus

2003

ChemInform

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Fused pyrimidine derivativesFused pyrimidine derivatives R 0515 Synthesis of Heterocyclic Systems by the Reaction of Zwitterionic Compounds with Isocyanates and Thiophosgene. -The usefulness of zwitterionic compounds (III) in the synthesis of pharmacologically interesting fused heterocyclic systems (V) and (VII) is described. -(ZALESKA*, B.; KARELUS, M.; Synlett 2002, 11, 1831-1834; Dep. Org. Chem., Jagiellonian Univ., PL-30-060 Krakow, Pol.; Eng.) -Mais 09-151

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Spectroscopic Study of the Conformation of 2-Anilino-2-ethoxy-3-oxothiobutyric Acid Anilides

Cited by 6 publications

References 0 publications

New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Synthesis of Heterocyclic Systems by the Reaction of Zwitterionic Compounds with Isocyanates and Thiophosgene.

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Spectroscopic Study of the Conformation of 2-Anilino-2-ethoxy-3-oxothiobutyric Acid Anilides

Cited by 6 publications

References 0 publications

New α-Amido-α-aminonitrones As Building Blocks for Constructing ­Heterocyclic Systems

New α-Amido-α-aminonitrones As Building Blocks for Constructing ­Heterocyclic Systems

A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Synthesis of Heterocyclic Systems by the Reaction of Zwitterionic Compounds with Isocyanates and Thiophosgene.

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New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems

New α-Amido-α-aminonitrones As Building Blocks for Constructing Heterocyclic Systems