Lactam acetals

Граник, В. Г.; Zhidkova, A. M.; Kuryatov, N. S.; Pakhomov, V. P.; Глушков, Р. Г.

doi:10.1007/bf00470348

Cited by 5 publications

(5 citation statements)

References 2 publications

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“…1 Н NMR spectra were registered on a Bruker 300 MHz spectrometer (TMS as a standard, DMSO-d6 as a solvent). 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine 4 was obtained by alkylating caprolactam with dimethyl sulfate using the method (Granik et al 1973) in a dry benzene. Hydrobromides of 2-hydrazino-4-arylthiazoles (3 a-d) were obtained by condensation of the corresponding phenacyl bromide (1 a-d) with thiosemicarbazide (2) by the method (Mazzone et al 1992).…”

Section: Methodsmentioning

confidence: 99%

The synthesis of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hydrazine hydrobromides and the cardioprotective activity of (41-methoxyphenyl-thiazol-2-yl) derivative

Demchenko¹,

Fedchenkova²,

Yeromina³

et al. 2021

PHAR

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A novel series of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3Н-azepin-2-yl)-hydrazine derivatives were synthesized by interaction of equimolar quantities of substituted α-bromacetophenones with thiosemicarbazide and characterized on the basis of their elemental analyses and spectral data. Study of cardioprotective activity of the all new products in comparison to levocarnitine and its synthetic analogue mildronate were carried out. Thus, specified results indicate, N-[(41-methoxyphenyl)-thiazol-2-yl)]-N1-(4,5,6,7-tetrahydro-3Н-azepin-2-yl)-hydrazine hydrobromide was influenced deceleration of contractive response of smooth muscles to hypoxia 13.2% more effective than levocarnitine and 6.85% more effective than mildronate and were shown pronounced cardioprotective properties. Obtained data justifies further study of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3Н-azepin-yl)-hydrazine derivatives as new potential cardioprotective drugs for treatment of various cardiac diseases.

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Section: Methodsmentioning

confidence: 99%

The synthesis of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hydrazine hydrobromides and the cardioprotective activity of (41-methoxyphenyl-thiazol-2-yl) derivative

Demchenko¹,

Fedchenkova²,

Yeromina³

et al. 2021

PHAR

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“…The diethoxy derivatives 97 were synthesized with yields of 40-60% as a result of treatment of the salts 96, formed during the reaction of lactams 1-3 with dimethyl sulfate, with sodium ethoxide in alcohol [6]. …”

Section: Reactions With Alcoholsmentioning

confidence: 99%

“…The heating of lactams with dimethyl sulfate [2][3][4][5][6][7][8][9][10][11][12][13][14][15], or more rarely diethyl sulfate [4,5,[15][16][17], is the most widely used method for the synthesis of lactim ethers (Table 1).…”

Section: Reactions Of Lactams With Dialkyl Sulfates or Trialkyloxoniumentioning

confidence: 99%

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Shvekhgeimer

2005

Chem Heterocycl Compd

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“…Ia and 1 ml of O-methylvalerolactim (II, n = 1) [9] was boiled for 1 h 45 min and cooled. The precipitate was separated by filtration and washed with petroleum ether to obtain 0.61 g of compound IVa.…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and neurothropic properties of 1-(2,6-dichlorophenyl)-3-amino(alkoxy)methyleneindolin-2-one

Graevsksya¹,

Ryabova²,

Алексеева³

et al. 1998

Pharm Chem J

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The presence of an active methylene unit in position 3 of the oxindole molecule provides for the ability of condensation of various reagents at this site. Previously we have demonstrated that dimethylformamide diethylacetal smoothly reacts with 1-(2,6-dichlorophenyl)indolin-2-one (Ia) and its derivatives with the formation of the corresponding enamines, the latter being the initial reagents for the synthesis of transamination products and condensed indoles [1][2][3]. In this work we have used a series of lactim esters, including Omethylvalerolactims (II, n = 1), O-methylcaptolactims (II, n = 2), orthoformic ester, and N,N-dimetylacetamide (III), as condensing agents.It was found that, in accordance with the commonly accepted notions [4], the amidacetals are much more reactive than the lactim esters and orthoesters. Indeed, the condensation process with amidacetals proceeds readily even at room temperature, while the interaction with lactim esters II requires boiling in the absence of solvent, and the reaction with orthoformic ester is possible on boiling in the presence of acetic anhydride. This order of reactivity is quite understandable since the behavior of amidacetals in the case under consideration is characterized by equilibrium involving ambidentate cations and alkoxy anions: Here, the anion acts as an acceptor of the 3-H proton of the indolinone cycle and the Ilia cation serves an electrophilic agent. The weakly basic lactim esters II are much less

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Lactam acetals

Cited by 5 publications

References 2 publications

The synthesis of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hydrazine hydrobromides and the cardioprotective activity of (41-methoxyphenyl-thiazol-2-yl) derivative

The synthesis of N-(4-aryl-thiazol-2-yl)-N1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-hydrazine hydrobromides and the cardioprotective activity of (41-methoxyphenyl-thiazol-2-yl) derivative

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Synthesis and neurothropic properties of 1-(2,6-dichlorophenyl)-3-amino(alkoxy)methyleneindolin-2-one

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