Synthesis and pharmacological activity of some 2, 5-dialkoxy-2-(dialkoxymethyl)tetrahydrofurans

Пересада, В. П.; Ostrovskaya, R. U.; Лихошерстов, А. М.; Rodionov, A. P.; Rozenberg, Sylvie; Сколдинов, А. П.

doi:10.1007/bf00762049

Cited by 3 publications

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“…3). The dihedral angles corresponding to the vicinal constants of these protons are about 30° and 150°, with the result that the geminal coupling constants are similar to the vic inal constants (8)(9)(10)(11). The dihedral angle between the bonds formed by the protons H(2b) (δ 3.45) and H(3a) (δ 3.58) with the corresponding carbon atoms is close to This situation is apparently attributed to the pseu doequatorial position of the substituent at the amine nitrogen atom (Fig.…”

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confidence: 85%

“…Starting 2,5 dimethoxy 2 dimethoxymethyltetrahydrofuran (5) was synthesized according to a known procedure. 11 Synthesis of methyl α α α α α (2 formyl 1H pyrrol 1 yl)carboxylates (4) (general procedure). 2,5 Dimethoxy 2 dimethoxymethyltet rahydrofuran (5) (51.56 g, 0.25 mol) was added to a solution of NaOH (11.0 g, 0.275 mol), H 3 PO 4 (16 mL, 0.275 mol), and amino acid methyl ester hydrochloride 6 (0.275 mol) in water (150 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Heterocycles 1-3 were synthesized starting from me thyl α (2 formyl 1H pyrrol 1 yl)carboxylates (4). We de veloped a new procedure for the synthesis of these com pounds based on the condensation of 2,5 dimethoxy 2 dimethoxymethyltetrahydrofuran (acetal 5) 11 with amino acid methyl ester hydrochlorides 6 in an aqueous phos phate buffer (pH 4.7) (Scheme 1). The five membered heterocycle in this reaction is formed due to the fact that in an acidic medium the hydrolysis of the starting acetal 5 containing three reaction centers initially occurs at the least stable endocyclic ketal group.…”

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Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]pyrazinones

et al. 2010

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Synthesis and selected properties of N substituted pyrrolo[2,1 c] 1,3 diazacycloalkano[1,2 a]pyrazinonesThe reactions of methyl α (2 formyl 1H pyrrol 1 yl)carboxylates with N substituted aliphatic 1,2 , 1,3 , and 1,4 diamines afford new pyrrole containing heterocyclic systems: 1,2,3,10b tetrahydroimidazo[1,2 a]pyrrolo[2,1 c]pyrazin 5(6H) ones, 1,3,4,11b tetrahydro 2H pyrrolo[2´,1´:3,4]pyrazino[1,2 a]pyrimidin 6(7H) ones, and 1,2,3,4,5,12b hexahydro pyrrolo[2´,1´:3,4]pyrazino[1,2 a][1,3]diazepin 7(8H) ones. The reduction of these compounds with different reagents was studied.* t 1 , 120-150 s; t 2 , 1 day; t 3 , 1 week. ** One isomer. Scheme 6R´ = Me, n = 1 (a); R´ = H, n = 2 (b) which was obtained by subtraction of the spectrum recorded within one week after the dissolution of crystalline compound 1j in CDCl 3 from the spectrum recorded immediately after the dissolution (CDCl 3 ), δ: 1.79 (d, H, H a (CH b )Ar, 2 J = 13.3 Hz); 2.77 (ddd, 1 H, H a C(2), 2 J 2a,2b = 12.0 Hz, 3 J 2a,3b = 11.4 Hz, 3 J 2a,3a = 8.7 Hz); 2.89 (ddd, 1 H, H b C(2), 2 J 2b,2a = 12.0 Hz, 3 J 2b,3b =8.0 Hz, 3 J 2b,3a = 2.1 Hz); 2.99 (d, 1 H, H b (CH a )Ar, 2 J = 13.3 Hz); 3.33 (ddd, 1 H, H a C(3), 2 J 3a,3b = 11.5 Hz, 3 J 3a,2a = 8.7 Hz, 3 J 3a,2b = 2.1 Hz); 3.47 (dd, 1 H, H a (CH b )Ph, 2 J = 14.0 Hz, 3 J = 4.2 Hz); 3.55 (ddd, 1 H, H b C(3), 2 J 3b,3a = = 11.5 Hz, 3 J 3b,2a = 11.4 Hz, 3 J 3b,2b = 8.0 Hz); 3.68 (dd, H b (CH a )Ph, 2 J = 14.0 Hz, 3 J = 4.2 Hz); 3.84 and 3.86 (both s, 3 H each, 2 OMe); 5.04 (t, 1 H, CHCH 2 Ph, 3 J = 4.2 Hz); 5.20 (s, 1 H, H(10b)); 6.21 (m, 1 H, H(10)); 6.39 (m, 1 H, H(9)); 6.54 (d, 1 H, H Ar (5), 3 J = 8.1 Hz); 6.67 (m, 1 H, H(8)); 6.74 (d, 1 H, H Ar (6), 3 J = 8.1 Hz); 6.90-7.11 (m, 6 H, Ph, H Ar (2)). The 1 H NMR spectrum of the second diastereomer of 1j, which was obtained by subtraction of the spectrum recorded immediately after the dissolution of crystalline compound 1j in CDCl 3 from the spectrum recorded within one week after the dissolution (CDCl 3 ), δ: 2.39 (ddd, 1 H, H a C(2), 2 J 2a,2b = 10.9 Hz, 3 J 2a,3b = 11.1 Hz, 3 J 2a,3a = 8.5 Hz); 3.05 (ddd, 1 H, H b C(2), 2 J 2b,2a = 10.9 Hz, 3 J 2b,3b =7.6 Hz, 3 J 2b,3a = 1.9 Hz); 3.22-3.39 (m, 4 H, CH 2 Ph, H a (CH b )Ar, H a C(3)); 3.59 (ddd, 1 H, H b C(3), 2

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]pyrazinones

et al. 2010

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“…Acetal I is readily prepared from accessible 2-furaldehyde [8]; it reacted with amino acids IIa-IIf to give the corresponding 2-(2-formyl-1H-pyrrol-1-yl)alkanoic acids IIIa-IIIf in high yield (Scheme 1). The optimal reaction conditions implied heating the reactants at a I-to-II molar ratio of 1.1 : 1 in boiling water over a period of 1 h; these conditions ensured 80-90% yield of acids IIIa-IIIf.…”

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Azacycloalkanes: XXXIX. New Syntheses of 1H-Pyrrole-1-carboxylic acid and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-one derivatives

et al. 2009

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New procedures have been developed for the synthesis of α-(2-formyl-1H-pyrrol-1-yl)-substituted carboxylic acids, α-(2-R-aminomethyl-1H-pyrrol-1-yl)-substituted carboxylic acids, and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-ones on the basis of furfurol and α-amino acids.* For communication XXVIII, see [1].We previously described methods for the synthesis of a series of 1,2-substituted pyrroles [2] and 3,4-dihydropyrrolo[1,2-a]pyrazines [3,4] and showed that some of these compounds exhibit cardiovascular [2] and psychotropic [5] activity. It is also known that the process of preparing food by heating is accompanied by formation of various pyrrole and pyrrolo[1,2-a]pyrazine derivatives from carbohydrates and proteins [6,7], and these compounds are introduced into human organism together with food. Therefore, target-oriented syntheses of such compounds are very important from the viewpoints of both search for new medical agents and elucidation of their biological effect in the nutrition process.In the present communication we report on new methods of synthesis of α-(2-formyl-1H-pyrrol-1-yl)-substituted carboxylic acids III, α-(2-R-aminomethyl-1H-pyrrol-1-yl)-substituted carboxylic acids IV, and pyrrolo[1,2-a]pyrazine derivatives V and VI from 2,5-dimethoxy-2-(dimethoxymethyl)tetrahydrofuran (I) and α-amino acids II. Acetal I is readily prepared from accessible 2-furaldehyde [8]; it reacted with amino acids IIa-IIf to give the corresponding 2-(2-formyl-1H-pyrrol-1-yl)alkanoic acids IIIa-IIIf in high yield (Scheme 1). The optimal reaction conditions implied heating the reactants at a I-to-II molar ratio of 1.1 : 1 in boiling water over a period of 1 h; these conditions ensured 80-90% yield of acids IIIa-IIIf. The amount of water depended on the solubility of the initial amino acid. The results of the reactions with optically active (R)-and (S)-α-alanines and racemic (RS)-α-alanine demonstrated that the proposed procedure can be successfully used for the preparation of individual stereoisomers. Acids IIIb and IIIc were characterized by similar (in absolute value) but opposite in sign specific rotations and similar melting points (mp 131-132°C), while racemic compound IIId melted at 110-112°C. Furthermore, a mixture of equal amounts of the (S)-isomer and (RS)-compound showed depression of the melting point (mp 107-108°C). The above data indicated that no racemization occurred during the synthesis of acids III.In order to elucidate the mechanism of formation of acids III, we examined the reaction of glycine (IIa) with 2-oxopentanedial (A) which was obtained by hydrolysis of acetal I with dilute hydrochloric acid. This reaction afforded only traces of acid IIIa, indicating that the condensation of glycine with tricarbonyl system A involves terminal carbonyl groups in the latter rather than those in the 1,4-positions. Presumably, the reaction of acetal I with amino acids II begins with hydrolysis of the least stable endocyclic ketal moiety in molecule I. Next follows condensation of the amino acid at the ketone carbonyl gr...

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New Method of Synthesis of 5,6-Dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines

Schindler¹,

Mokrov²,

Лихошерстов³

et al. 2008

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Synthesis and pharmacological activity of some 2, 5-dialkoxy-2-(dialkoxymethyl)tetrahydrofurans

Cited by 3 publications

References 4 publications

Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]pyrazinones

Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]pyrazinones

Azacycloalkanes: XXXIX. New Syntheses of 1H-Pyrrole-1-carboxylic acid and 1,2-dihydropyrrolo-[1,2-a]pyrazin-3(4H)-one derivatives

New Method of Synthesis of 5,6-Dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines

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