Three-Component Spiro Heterocyclization of Pyrrolediones with Aminoindenones. Synthesis of Spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-pyrroles]

Russian Journal of Organic Chemistry - 4,5-Dibenzoyl-1H-pyrrole-2,3-diones and 4-benzoyl-5-phenyl-1H-pyrrole-2,3-diones reacted with 3-arylamino-1H-inden-1-ones at a molar ratio of 1:2 to give...     

γ-Fe2O3@SiO2@4-(sulfoamino)butanoic acid as a novel superparamagnetic nanocatalyst promoted green synthesis of 5-(aryl)-5H-spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-trione derivatives

Research on Chemical Intermediates - Grafting of 4-(sulfoamino)butanoic acid on superparamagnetic γ-Fe2O3@SiO2 nanoparticles afforded γ-Fe2O3@SiO2@4-(sulfoamino)butanoic acid as a novel...     

A novel three-component method for the synthesis of spiro[chromeno [4′,3′:4,5] pyrimido[1,2-b] indazole-7,3′-indoline]-2′,6(9H)-dione

A green, efficient, and rapid procedure for the synthesis of novel spiro[chromeno[4′,3′:4,5] pyrimido[1,2-b]indazole-7,3′-indoline]-2′,6(9 H)-dione derivatives has been developed by one-pot condensation of 4-hydroxy-2H-chromen-2-one, isatin, and 1H-indazole-3-amine, in the presence of acetic acid in EtOH. This method has the advantages of operational simplicity, and high yield of products via a simple experimental and work-up procedure as compared to the conventional methods. The reaction mechanism and substrate scope of this novel reaction is briefly discussed.     

Synthesis of Angular [1,2,5]Oxadiazolo[3,4-b]pyrazino-[1′,2′ : 1,2]pyrrolo[2,3-e][1,4]diazepine by Stepwise Reaction of Pyrrolo[1,2-a]pyrazinetrione with 3,4-Diaminofurazan

Russian Journal of Organic Chemistry - Diaminofurazan reacted with 8-benzoyl-2-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-1,6,7(2H)- trione to give addition product of the amino group to the double...     

A novel, fast and efficient one-pot four-component procedure for preparation of some alkyl spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizine]-2′-carboxylates

In this study we report a novel one-pot reaction which stereoselectively affords alkyl spiro[indeno[1,2-b]quinoxaline-11,3′- pyrrolizine]-2′-carboxylates via the four-component condensation of ninhydrin, phenylenediamines, proline, and acrylic acid derivatives. The reactions were run in ethanol and completed at less than 25 min and the products were obtained in very good yields. The stereochemistry of the products was deduced on the basis of the ¹H NOESY and comparison with the related systems.     

Electronic structure of diindeno[1,2,3-cd:1′,2′,3′-lm]perylene radical anion

The electronic structure of diindeno[1,2,3-cd:1′,2′,3′-lm]perylene (periflanthene) radical anion has been studied on the basis of the ESR, electronic absorption, and linear dichroism spectra. The observed results are interpreted in terms of the SCF MO calculations within the framework of the π-electron approximation.     

One-pot,three-component synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrroles] via the Hantzsch-type reaction of 1H-pyrrole-2,3-diones

A new methodology for the synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrrole] derivatives via a Hantzsch-type reaction has been developed. This process involves the one-pot, three-component reaction of a 1H-pyrrole-2,3-dione, an aminocyclohexenone and 1,3-indanedione in acetic acid at reflux. Operationally simple, metal-free reaction conditions, simplicity of product isolation and good yields are key advantages of this methodology.     

One-pot four-component domino reaction for the synthesis of bifunctionalized spiro[indazolo[3,2-b]quinazoline-7,3′-indoline hybrids: A green approach

An efficient tandem route to obtain novel spiro[indazolo[3,2-b]quinazoline-7,3′-indolines has been explored. The one-step domino reaction proceeds via in situ generation of the 1H-indazol-3-amines followed by its reaction with the cyclic 1,3-dicarbonyls and isatin derivatives to furnish complex N-fused spiro-polyheterocyclic frameworks. This protocol describes a valuable route to concisely and feasibly obtain spiro[indazolo[3,2-b]quinazoline-7,3′-indolines from isatin derivatives. The present protocol is particularly attractive because of the following features: group-assisted-purification (GAP) chemistry process, low-cost solvent, convenience of operation, excellent atom economy, and high yields.     

La(OTf)3-catalyzed,three-component synthesis of spiro[Indolo-3,10′-indeno[1,2-b]quinolin]-2,4,11′-triones in PEG-400 under conventional heating and ultrasonic irradiation

An efficient La(OTf)₃-catalyzed three-component reaction has been developed for the synthesis of highly substituted spiro[indolo-3,10′-indeno[1,2-b]quinolin]-2,4,11′-triones in polyethylene glycol (PEG-400) under conventional heating and ultrasonic irradiation. The most exciting feature of this methodology is its mechanism involving the unusual ring opening of an isatin moiety followed by recyclization. All the reactions resulted in good yield of products. The important features of this reaction are use of green solvent, good yields, less reaction times, and recyclability of the catalyst.     

Synthesis of novel spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d]pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones via three component reaction

A new and efficient method for the synthesis of hitherto unreported spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d]pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones was developed via the Domino Knoevenagel condensation–Michael addition–intermolecular cyclization sequences of isatin derivatives, cyclohexane-1,3-diones, and 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ones, employing 12-tungstophosphoric acid (H₃PW₁₂O₄₀) as an effective and inexpensive catalyst.     

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.     

New convenient synthesis of substituted 6,9-dihydropyrido[3′,2′:4,5]thieno[3,2-b]pyridines and 6,9-dihydropyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines

1,4-Dihydro-3-cyano-2-pyridinethiolates react with 2-bromo-l-(4-bromophenyl)ethylidenemalononitrile or N-cyanochloracetanudine to give 6, 9-dihydropyrido[3, 2': 4, 5]thieno[3. 2-b]pyridines or 6, 9-dihydropyrido-[3.2:4.5Jthieno(3,2-d]pyrimidines, respectively.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 553–556, April, 1996.     

Green synthesis and anticancer activity of tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridines catalyzed by phospho sulfonic acid

Biologically portent/significant tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridines are synthesized by an efficient green synthesis of various aldehydes with 3-methyl-1H-pyrazol-5(4H)-one in ammonium acetate using phospho sulfonic acid as a solid catalyst under microwave-assisted interaction under solvent-free conditions at 70°C. This methodology is easy to handle and get good to excellent yields. Later the potential in vitro antiproliferation of the titled compounds is evaluated. Among all the titled compounds, 4s and 4t showed the most potent anticancer potentiality on the used cancer cell lines of SK-BR-3 and HeLa (IC₅₀ = 10.70 ± 0.27 and 12.58 ± 0.38, and 19.38 ± 0.32 and 21.55 ± 0.41 μg/mL for SK-BR-3 cells lines and HeLa cells lines, respectively), which were comparable to the positive control.     

The synthesis and molecular recognition study of β-cyclodextrin derivatives modified by spiro[2H-benzopyran-2,2′-indoline]

Introduction

Encapsulation of rifampicin by β-cyclodextrin and its methyl and hydroxy-propyl derivatives was studied in solid and solution phase.

Materials and Methods

The inclusion phenomenon was evidenced by differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD) analysis and fourier-transform infrared (FT-IR) spectroscopy and supplemented by proton nuclear magnetic resonance (¹H-NMR) spectroscopy. The host–guest stoichiometry (1:1) and stability constant were determined by solution calorimetry.

Results

The inclusion of drug was found to be exothermic process accompanied by small negative value of Gibbs free energy (ΔG°) and small positive value of entropy (ΔS°).

Conclusion

The magnitude of equilibrium constant (K) indicates that methyl-β-cyclodextrin has the best complex formation ability. Solubility, dissolution and partition coefficient studies also support the most effective behavior of methyl-β-cyclodextrin.     

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.     

Synthesis and antitumor evaluation of novel tetrahydrobenzo[4′,5′]thieno[3′,2′:5,6]pyrimido[1,2-b]isoquinoline derivatives

In the present study, a novel 8,9,10,11-tetrahydro-7H,14H-benzo[4′,5′] thieno[2′,3′:4,5]-1,3-oxazino[3,2-b]isoquinoline-7,14-dione 5 was prepared by condensation of 2-amino-3-carbethoxy-4,5,6,7-tetrahydrobenzothiophene with homophthalic anhydride under microwave irradiation, followed by alkaline hydrolysis and cyclization using acetyl chloride. Compound 5 was further allowed to react with different nitrogen nucleophiles to get new tetrahydrobenzothienopyrimido isoquinolinone derivatives. The structures of the prepared compounds were elucidated by IR, ¹H-NMR, ¹³C-NMR, and mass spectroscopy. The newly prepared compounds were tested in vitro against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, and mammary gland breast MCF-7. Almost all the tested compounds showed satisfactory activity.     

Green Aspect for Multicomponent Synthesis of Spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles]

An efficient, four-component reaction of isatin, 1,3-indanedione, ethyl acetoacetate, and ammonium acetate in ethanol/water (9:1) system furnished spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles] at room temperature. Merits of the method are mild reaction conditions, simple workup procedure, and ambient temperature. The synthesized compounds exhibit excellent fluorescence properties.     

Synthesis of novel tricyclic 2H,7H-furo[3′,4′:6,7]cyclohepta-[1,2-b]pyran system

The reaction of 8-hydroxy-1,3-dimethyl-4H-cyclohepta[c]furan-4-one with the ethoxymethylene derivatives of malononitrile or ethyl cyanoacetate in the presence of KOH gave noncyclic cyanovinyl derivatives as their potassium salts rather than the expected α-pyrone derivatives. They are smoothly cyclized to the target α-pyrones by refluxing with acid. The corresponding 3-benzamido-2H-pyran-2-ones can be obtained in a single vessel from the 2-aryl-4-ethoxymethylene-4H-1,3-oxazol-5-ones using the same scheme. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1632–1638, November, 2008.     

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.