Synthesis of Dispiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo-[2,1-a]isoquinoline-3′,3′′-indolin]-2′′-one Derivatives via Cycloaddition Reactions

Russian Journal of General Chemistry - The 1,3-dipolar cycloaddition reaction of (Z)-1-aryl-2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)ethan-1-one with generated in situ azomethine ylide leads to...     

One-Pot Synthesis of Thieno[2,3-b]pyridine and Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine Derivatives

Russian Journal of Organic Chemistry - 2-Acyl-4,5,6-trialkyl-3-aminothieno[2,3-b]pyridines,...     

Synthesis of New Derivatives Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine

Russian Journal of Organic Chemistry - The reactions of 4-methyl- and (RS)-4,6-dimethyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo-[2′,1′:6,1]pyrido[2,3-d]pyrimidines and...     

Novel Synthesis of Pyrano[2,3-d]Thiazole,Thiazolo[3,2-a]Pyridine,and Pyrazolo [3′,4′:4,5] Thiazolo[3,2-a]Pyridine Derivatives

Cyclocondensation of 2-cyanomethyl-4-thiazolidinone (1) with tetracyanoethylene (2) furnished pyrano[2,3-d]thiazole derivative (4) . Benzo[e]pyrano[2,3-d]thiazole derivative (6) was obtained by cyclization of compound (1) with salicylaldehyde. In a similar manner, condensation of compound (1) with 2-hydroxy-1-naphthaldehyde in refluxing ethanol yielded naphtho[e]pyrano[2,3-d]thiazole derivative (7) . Interaction of compound (9) with benzylidenemalononitriles (10) (1 : 1 molar ratio) at reflux temperature in ethanol in the presence of piperidine afforded thiazolo[3,2-a]pyridines (12a-c) . Treatment of compound (12a) with hydrazines furnished pyrazolo[3′,4′:4,5] thiazolo[3,2-a]pyridines (14a,b) . The reaction of compound (1) with benzyli-denecyanoacetate (16) yielded 5-hydroxythiazolo[3,2-a]pyridine derivative (21) . Cyclization of bis(thiazolinone) (23) with benzylidenemalononitriles (10) produced bis(thiazolopyridine) derivatives (25a,b) .     

Simple Analogues of Acyclonucleosides: Synthesis of N‐Substituted Pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine Derivatives

The synthesis of N‐substituted pyridothienopyrimidines bearing ethoxymethyl, benzyloxymethyl, methylthiomethyl, benzoylmethyl, allyl, sec‐butyl, and 2‐acetyloxyethyl chains as a sugar mimic was described. The O‐substituted pyridothienopyrimidines were obtained during some reactions.     

Studies of Thiazolopyridines,Part 6: Synthesis and Antimicrobial Evaluation of Some Novel Thiazolo[3,2-a] Pyridine and Thiazolo[2′,3′:6,1]-pyrido[2,3-d]pyrimidine Derivatives

Condensation of thiazolinone 1 with aromatic aldehydes yielded the corresponding methylidene derivatives 2a–f. Cyclization of compounds 2a–f with arylidenemalononitrile 3 (1:1 molar ratio) in ethanol in the presence of piperidine furnished the novel thiazolo[3,2-a]pyridines 5a–v, via Michael adduct 4. Compounds 5p, r were cyclized with malononitrile in the presence of piperidine to yield thiazolo[3,2-a][1,8]naphthryidines 7a, b. Thiazolo-[2′,3′:1,6]pyrido[2,3-d]pyrimidine 9a–cwere obtained by cyclization of compounds 5c, p, r with formic acid. The structure of the synthesized compounds was established by analytical and spectral data. Also, some of the synthesized compounds were screened for antimicrobial activity in vitro.     

Synthesis of New Polycyclic Compounds Containing Thieno[2′,3′:5,6]pyrimido[2,1-a]isoindole Fragment

Russian Journal of General Chemistry - The reaction of partially saturated derivatives of 3-aminothieno[2,3-b]pyridine-2-carboxamide with phthalic anhydride in acetic acid or DMF on heating leads...     

Synthesis of spiro[furan-3,3′-indolin]-2′-ones by PET-catalyzed [3+2] reactions of spiro[indoline-3,2′-oxiran]-2-ones with electron-rich olefins

An efficient procedure for the synthesis of spiro[furan-3,3′-indolin]-2-ones and dispiro[cycloalkane-1,2′-furan-3′,3″-indolin]-2″-ones has been achieved in high yields and stereoselectivity by photoinduced electron transfer-catalyzed [3+2] reactions of substituted spiro[indoline-3,2′-oxiran]-2-ones with olefins. The reactions proceed by ring opening of spiro[indoline-3,2′-oxiran]-2-ones via C_β–O bond cleavage and subsequent cycloaddition with olefins by using 2,4,6-triphenylpyrylium tetarfluoroborate (TPT) as a sensitizer.     

Synthesis and reactions of new 4-chloro-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]-benzimidazoles

Summary 4-Chloro-2-methylpyrimidino[4,5:4,5]thiazolo[3,2-a]benzimidazole (3) was prepared by chlorination of2 which could also be converted directly to 2-methylpyrimidino[4,5:4,5]-thiazolo[3,2-a]benzimidazol-4-thiol (4). Nucleophilic substitution of3 with alcohols, phenols, primary amines, secondary amines, sodium azide, and mercaptoacetic acid gave the corresponding derivatives. The thiol derivative4 was reacted with alkyl/aralkyl halides, phenacyl bromide derivatives, bromoacetone, chloroanilides, bromomalonic ester, and ethyl bromoacetate to afford compounds of potential pharmacological interest.

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Synthese und Reaktionen neuer 4-Chlor-2-methylpyrimidino[4,5:4,5]thiazolo[3,2-a]benzimidazole

Zusammenfassung 4-Chlor-2-methylpyrimidino[4,5:4,5]thiazolo[3,2-a]benzimidazol (3) wurde durch Chlorierung von2, welches auch direkt zu 2-Methylpyrimidino[4,5:5,4]thiazolo[3,2-a]-benzimidazol-4-thiol (4) umgesetzt werden kann, hergestellt. Nucleophile Substitution von3 mit Alkoholen, Phenolen, primären Aminen, sekundären Aminen, Natriumazid und Mercaptoessigsäure ergab die entsprechenden Derivate. Das Thiolderivat4 wurde mit Alkyl/Alkarylhalogeniden, Phenacylbromidderivaten, Bromaceton, Chloraniliden, Brommalonsäureester und Bromessigsäureethylester zu potentiell pharmakologisch interessanten Verbindungen umgesetzt.

     

Thieno[2,3-b]pyridine-2-carbohydrazide in Polyheterocyclic Synthesis: The Synthesis of Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine,Pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine,and Pyrazolyl,Oxadiazolylthieno[2,3-b]pyridine Derivatives

Pyrdine-2(1H)-thione 1 reacted with ethyl chloroacetate 2 to give 2-S-ethoxy-carbonylmethylpyridine derivative 3, which could be cyclized into thieno[2,3-b]-pyridine-2-carbohydrazide derivative 5 by boiling with hydrazine hydrate. The latter compound reacted with cinnamonitrile derivatives 6a, b, triethylorthoformate, formic acid, dimethylformamide-dimethylacetal, and diethyl carbonate to give the corresponding shiff base 7a, b and pyrido[3′,2′;-4,5]thieno[3,2-d]pyrimidine derivatives 10–13 in respective manner. On the other hand, compound 5 also reacted with carbondisulphide and phenyl isothiocyanate to afford the corresponding 2-(1,3,4-oxadiazolo-2-yl)thieno[2,3-b]pyridine derivatives 18 and 22. Finally, compound 5 reacted with some β-dicarbonyl compounds, such as ethyl acetoacetate, acetylacetone and ethyl β-arylazoacetoacetate, to yield the corresponding 2-(pyrazol-1-yl-carbonyl)thieno[2,3-b]pyridine derivatives 24, 25, and 27 respectively.     

Design, Synthesis, and Hypnotic Activity of Pyrazolo [1,5-a]pyrimidine Derivatives

On the basis of the Zaleplon structure, novel pyrazolo[1,5-a]pyrimidines were designed and prepared for studies on their hypnotic activity. This paper reported the synthesis of twelve new 5-methyl-7-substituted-pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivatives by using simple starting materials such as propane dinitrile and triethyl orthoformate. The structures of the derived target compounds were confirmed by their IR and ^1H-NMR spectroscopic data. The preliminary pharmacological evaluations indicated that some compounds showed hypnotic activity, whilc derivative 1c was the most potent one.     

Synthesis of a new heterocyclic system of 2-amino-3-cykanO-5h-4,5-dihydropyrido[3′,2′:4,5]-pyrrolo[1,2-a]indole

Alkylatio of 2-piperidinomethylene-2H-pyrrolo[1,2-a]indole-3,9-dione with dimethyl sulfate, followed by hydrolysis of the intermediate immonium salts. yielded 2-formyl derivatives, the reaction of which with substances possessing on active methylene unit leads to the formation of 2-substituted vinyl-3-oxo-9-alkoxypyrrolo[1,2-aindoles. Cyclization of the 9-methoxy derivative yielded a new heterocyclic system of 2-amino-3-cyano-5H-4,5-dihydropyrodol[32:4,5]pyrroloindoledione-4,11.Center for the Chemistry of Drugs, S. Ordzhonikidze All-Russian Scientific Research Institute Moscow119021 Translated from Khimiya Geterotsiklicheskikh Soedinenii.No. 8, pp, 919–925, August, 1994. Orginally article submitted June 22, 1994.     

Synthesis of chromeno[2′,3′:4,5]imidazo[2,1-a]isoquinolines via a novel domino reaction of isoquinoline-derived immonium salts. Scope and limitations

A one-pot protocol towards chromeno[2′,2′:4,5]imidazo[2,1-a]isoquinoline derivatives via a domino reaction of isoquinoline-derived immonium salts and α-hydroxy aromatic aldehydes is elaborated. The scope and limitations of this reaction is discussed.     

Synthesis and Crystal Structure of 3′-Ethyl 5′-Methyl 1-Benzyl-4′-methyl-2-oxo-3′,4′-dihydrospiro-[indoline-3,2′-pyrrole]-3′,5′-dicarboxylate

The crystal structure of the title compound(C24H24N2O5, Mr = 420.45) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P1 with a = 8.991(1), b = 11.166(1), c = 11.169(1) , α = 91.413(2), β = 105.887(2), γ = 90.992(2)°, V = 1077.8(2) 3, Z = 2, Dc = 1.296 g/cm3, F(000) = 444, μ(MoKα) = 0.091 mm-1, the final R = 0.0466 and wR = 0.1507 for 4185 observed reflections(I 2σ(I)). The single-crystal X-ray diffraction data indicated intermolecular C(17)–H(17)O(4), C(5)–H(5)… O(4) hydrogen bonds and C–H…π interaction in the structure.     

Dipyrrolo[1,2-a; 2′,1′-c]pyrazines. 5. Azo coupling of dipyrrolo[1,2-a;2′,1′-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a; 2′,1′-c]pyrazines

We have synthesized a series of previously unreported azo dyes via the azo coupling of alkyl substituted dipyrrolopyrazines with aryldiazonium chloride. For this type of substrate where one or both -positions of the pyrrole rings of the molecules are not occupied by substituents, electrophilic attack was found to occur initially at carbon atom C₍₃₎.For communication 4 see [1]M. V. Lomonosov State University, Moscow 119899, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 236–240, February, 1999.     

Dipyrrolo[1,2-a; 2′,1′-c]pyrazines. 4. Aminomethylation of alkyl substituted dipyrrolo[1,2-a; 2′,1′-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a; 2′,1′-c]pyrazines

We have studied the aminomethylation reaction of alkyl substituted dipyrrolo[1,2-a; 2,1-c]pyrazines and their 5,6-dihydro analogs using different aminomethylating agents. Use of alkoxydialkylaminomethanes (aminoacetals) as Mannich reagents leads to the highest yields of the aminomethylated dipyrrolopyrazines. The compounds prepared have been studied by mass spectrometry.For Communication 3, see [1].M. V. Lomonosov State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 949–957, July, 1998.     

Catalyst-free glycerol-mediated green synthesis of 5′-thioxospiro[indoline-3,3′-[1,2,4]triazolidin]-2-ones/spiro[indoline-3,3′-[1,2,4]triazolidine]-2,5′-diones

The development of new catalyst-free green and efficient protocol to access 5′-thioxospiro[indoline-3,3′-[1,2,4]triazolidin]-2-ones/spiro[indoline-3,3′-[1,2,4]triazolidine]-2,5′-diones, potential privileged scaffolds for drug discovery, is disclosed. Key feature of this methodology is the dual use of glycerol—a recyclable, bioorganic compound, as a solvent cum promoter. Other highlights include use of inexpensive reagents, mild reaction conditions, operational simplicity, short reaction time, no need for chromatographic purification, and high yields.     

Synthesis of derivatives of pyrido[3′,2′:4,5]furo[3,2-c]isoquinoline heterocyclic system

An approach to the synthesis of derivatives of new heterocyclic system, pyrido[3′,2′:4,5]-furo[3,2-c]isoquinoline, was suggested. A condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation product with potassium tert-butoxide leads to substituted pyrido[3′,2′:4,5]furo[3,2-c]-isoquinolin-5(6H)-ones. Similarly, a condensation reaction of substituted 3-cyanopyridin-2(1H)-ones with 2-(chloromethyl)benzonitrile and subsequent treatment of the condensation product with potassium tert-butoxide gives substituted 5-aminopyrido[3′,2′:4,5]furo[3,2-c]-isoquinolines.     

Synthesis of Novel Polycyclic Carbamate Derivatives of 2-Hydroxy-2,2′-biindane-1,1′,3,3′-tetrone

Russian Journal of Organic Chemistry - Methyl 1,3,11′-trioxo-1,3,10a′,11′-tetrahydro-4β′H-spiro[inden-2,10′-indeno[1,2-b]chromene]-7′(8′)-ylcarbamates...     

Construction,characterization, and antimicrobial evaluation of the novel heteroannulated chromeno[2′′,3′′:6′,5′]pyrido[2′,3′-d] [1,3] thiazolo[3,2-a]pyrimidines

The reaction of chromone-3-carbonitrile with thiobarbituric acid afforded 2-thioxochromeno[3′,2′:5,6]pyrido[2,3-d]pyrimidine-4,6(1H,3H)-dione, which utilized as a building block for construction of a novel heteroannulated compounds containing chromenopyridothiazolopyrimidine moiety. Reactions of the starting compound with a variety of bielectrophilic reagents namely; chloroacetonitrile, bromomalononitrile, 3-chloropentanedione, ethyl 2-chloro-3-oxobutanoate, phenacyl bromide, chloroacetic acid, dibromoethane, and oxalyl chloride afforded the first known chromenopyridothiazolopyrimidines. Cyclization of the starting compound with 2,3-dichloroquinoxaline gave the linear hepta-annulated chromenopyridopyrimidothiazoloquinoxaline. In addition, chromenopyridopyrimido thiazolopyrimidines were efficiently synthesized. The antimicrobial activity was evaluated for the prepared compounds and some of them seemed notable activity against the tested microorganisms. Analytical and spectral data confirmed the structures of the new products.