Derivatives Of Pyrido Research Articles

Synthesis, anti-inflammatory and analgesic activity of pyrido[2,1-b]quinazoline derivatives

Derivatives of pyrido[2,1-b]quinazoline were synthesized by reacting 2-chloronicotinic acid, its nitrile and amides with anthranilic acid or 2-aminotriphenylcarbinol. The anti-inflammatory and analgesic activity of the compounds was studied.

The Stereochemistry of Organometallic Compounds. XLII. The Preparation of [2,1-b]Quinazolines Involving Rhodium-Catalysed Hydroformylation of 2-Amino-N-Alkenylbenzylamines

Rhodium-catalysed reactions of 2-amino-N-alkenylbenzylamines with H2/CO give hexahydro-pyrrolo- and hexahydropyrido -[2,1-b] quinazolines. Reactions of N-allyl derivatives give a single regioisomer, and reactions of but-3-enyl analogues give mixtures of pyrrolo and pyrido derivatives. Some reactions give significant amounts (10-30%) of tetrahydro derivatives. The origin of these compounds remains unclear.

ChemInform Abstract: Synthesis, Characterization and Antimicrobial Evaluation of Thione and Dithione Derivatives of Pyrido(2,3‐d)pyrimidines.

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The Stereochemistry of Organometallic Compounds. LXI. The Preparation of Quinazolines and Quinazolinones Involving Rhodium-Catalyzed Hydroformylation of Alkenyl Anilines

Rhodium-catalysed reactions of ortho-alkenylaminobenzylamines or benzamides with H2/CO give quinazolines and quinazolinones containing a fused alicyclic ring in excellent yields. Reactions of N- allyl derivatives give a single regioisomer. Reactions of but-3-enyl analogues give readily separable mixtures of pyrrolo and pyrido derivatives. Their 3-methylbut-3-enyl analogues give the pyrido derivatives (12) and (13) in reactions which show unusual diastereoselectivity.

Synthesis of derivatives of pyrido[2,3-d]pyrimidines condensed with tetrahydropyran and tetrahydrothiopyran

Methods have been developed for obtaining derivatives of W-amino(oxo)-, 8,10-dioxo-, and 10-amino-8-oxo(thio)pyrano(thiopyrano) [4′,3′:4,5]pyrido[2,3-d]pyrimidine on the basis of 3-amino(benzylamino)-4-cyano (carbamoyl)pyrano(thiopyrano)[3,4-c]-pyridines.

Synthesis of functionalized pyrimidine-4-thiones and derivatives of pyrido[2,3-d]pirimidine-5-one from monoacylketene aminals

Monoacylketene aminals containing an unsubstituted NH2 group react as C-nucleophiles with benzoyl isothiocyanate to give the corresponding thioamides which undergo cyclization by sodium methoxide in methanol to afford 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones. A scheme for constructing the pyrido[2,3-d]pyrimidine system from keteneaminals is offered. The reaction of 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones with dimethylformamide dimethylacetal leads to 8-R-N-4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-ones. Cyclization of 5-acetyl-6-benzoylamino-4-methylthio-2-phenylpyrimidine by sodium methoxide yields N-unsubstituted 4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-one.

Zur Synthese von Derivaten des Pyrido[1,2‐a]azepins

On the Synthesis of Derivatives of Pyrido[1,2‐a]lazepineThe conjugated pyridinium ylides of type 4 undergo 8π ‐electrocyclisation affording the heterobicyclic allenes 5 which, in the presence of H2O and H2O2, are subsequently transformed into the substituted pyrido[1,2‐a]‐azepinones 6, a novel heterocyclic system. The chemical behaviour of 6a,b is dominated by cleavage of the lactam bond and subsequent reaction to pyridinc and isoquinoline derivatives, respectively; e.g. reaction of 6a, b with 4,5‐dihydro‐4‐methyl‐3H‐1,2,4‐triazole‐3,5‐dione affords the cycloadducts 11 and 12 almost quantitatively. The successful transformation of 6b into 15 is described, the latter being the first representative of the presently unknown, potentially antiaromatic pyrido[1,2‐a]azepine (1).

Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. An attempt to prepare benzoylamino substituted azolo‐ and azinopyrimidines with a bridgehead nitrogen atom

AbstractMethyl 2‐benzoylamino‐3‐dimethylaminopropenoate (2) was introduced as a new reagent for the preparation of fused pyrimidinones 4 from heterocyclic α‐amino compounds in acetic acid. In this manner, derivatives of pyrido[1,2‐a]pyrimidine 4a,b,f, pyrimido[1,2‐b]pyridazine 4g, pyrimido[1,2‐c]pyrimidine 4j, pyrazino[1,2‐a]pyrimidine 4k, thiazolo[2,3‐b]pyrimidine 41, pyrazolo[1,5‐a]pyrimidine 4m, and 1,2,4‐triazolo‐[1,5‐a]pyrimidine 4n were prepared.

Eine einstufige Synthese von Azolo-anellierten Derivaten des Pyrido[2,3-d]pyrimidins

A One-Pot Synthesis of Azolo-annulated Derivatives of Pyrido[2,3-d]pyrimidine 6-Nitro[1,2,4]triazolo- and 6-nitropyrazolo[1,5-a]pyrimidines 1a-h react with malononitrile and ethyl cyanoacetate to yield 9-imino-, 2a-h, and 9-oxo-7-nitro-4,9-dihydroazolo[1,5-a]pyrido-[2,3-d]pyrimidines 4a-g, respectively. By using the N*C*-double-labelled ethyl cyanoacetate in this reaction, its participation as a 1,3-bifunctional reagent was established. Malononitrile or ethyl cyanoacetate provide the C-C-N fragment for the pyridine ring. The mechanism is discussed.

Quantum mechanical studies on the activity of anticancerous drug — Ellipticine

Ellipticine compounds, derivatives of pyrido-(4-3b) carbazole are used in the human cancer therapy. Most of these drugs interact directly with DNA molecule. CNDO method, alongwith second order perturbation theory and multicentered-multipole approxiation have been used to compute intermolecular interaction energies of ellipticine with DNA ase pairs (GC and AT) in both normal and inverted cases. An attempt has been made to correlate the drug-nucleic acid interactions for ellipticine to locate site of drug action and binding pattern on the basis of intermolecular forces

Synthesis and properties of 3-aminomethyl derivatives of 3H-2-imino-7-methyl-4-oxopyrido-[3,2-e]-1,3-thiazine-5- and -6-carboxylic acids.

It was stated that esters of 3H-2-imino-7-methyl-4-oxopyrido [3,2-e]-1,3-thiazine-5- and -6-carboxylic acids (I, II) undergo the Mannich reaction giving the corresponding 3-aminomethyl derivatives (III-XIV). Derivatives of ester II [(XII) and (XIV)] showed distinct analgesic and antiserotonic activities.

ChemInform Abstract: THE SYNTHESIS AND COLOR OF PYRIDO(1′,2′:1,2)PYRIMIDO(4,5‐B)ACRIDINE‐7,15‐DIONES

AbstractDie Titelverbindungen (VII) werden durch Dehydrierung der auf zwei verschiedenen Wegen erhältlichen Dihydroderivate (III) dargestellt.

Acetals of lactams and acid amides. 39. Synthesis of three-ring derivatives of pyrido [l,2-a] pyrimidines on the basis of the reaction of dimethylformamide acetal with dicyanomethylenecycloalkanes

The reaction of dicyanomethylenecyclopentane and -cyclohexane with dimethylformamide diethylacetal was used to synthesize dieneamino nitriles, from which isoquinoline and 2-pyridine derivatives were obtained by treatment with ammonia. The reaction of 3-aminopyridine and 3-aminoisoquinoline derivatives with ethoxymethylenemalonic ester leads to pyrimido [l,2-b] isoquinoline and -2-pyrindene derivatives.

The Synthesis and Color of Pyrido[1′,2′ : 1,2]pyrimido[4,5-b]acridine-7,15-diones

Abstract Some derivatives of pyrido[1′,2′: 1,2]pyrimido[4,5-b]acridine-7,15-diones have been synthesized, their absorption spectra have also been investigated in order to elucidate the relationship between the color and the chemical constitution in contrast to the related compounds, quinacridone and pyrido[2,1-b]pyrido[1′,2′ : 1,2]pyrimido[4,5-g]quinazoline-7,15-dione. The absorption spectra in DMSO and in concentrated sulfuric acid show a good correlation with the electronic effect of the substituents. The absorption spectra of the solid are more influenced by the position of the substituents than by the electronic effect.

Synthesis of indole derivatives of pyrido[2,3-d]pyrimidine

Recyclization of the pyrimidine ring with inclusion of the reagent in the newly formed ring to give indole derivatives of 2,3-disubstituted pyridines occurs in the reaction of the anhydro base of 4-(3-indolyl)pyrimidine with CH acids in the presence of triethylamine. The products react with formamide to give the pyrido[2,3-d]pyrimidine heterocyclic system.

Investigation of nitrogen- and sulfur-containing heterocycles. 39. Reactions of 2-mercapto-3-ureido- and 2-mercapto-3-aminopyridines with ?-halo carbonyl compounds. Synthesis of 6-oxo derivatives of pyrido[2,3-b][1,5]thiazepines

The reaction of 2-mercapto-3-ureido- and 2-mercapto-3-aminopyridines with β-halo derivatives of carbonyl compounds (ketones, acids, and aldehydes) and with acrylonitrile proceeds not only via the mercapto group but also via the amino group, as a result of which S-β-keto (carboxy, cyano) alkyl, N,S-bis(β-ketoalkyl), and N,S-diacyl derivatives of pyridine are formed. The action of acids, alkalis, and dehydrating agents on 2-S-β-keto (carboxy, cyano) ethyl-3-aminoureidopyridines was studied. A method for the preparation of derivatives of a new heterocyclic system, viz., 6-oxopyrido [2,3-b] [1,5] thiazepine, by the reaction of 2-mercapto-3-aminopyridines with β-bromopropionic acid and subsequent treatment of 2-(β-car-boxyethyl) thio-8-aminopyridines with dicyclohexylcarbodiimide was developed.

Condensed heterocyclic systems with a quaternary nitrogen atom

Nitro and amino derivatives of pyrido[1,2-f]phenanthridinium perchlorate were synthesized by the Pschorr method and by photocyclodehydrogenation from N-(nitrophenyl)-or N-(aminophenyl)pyridinium perchlorates. The mechanism of the photoconversion was investigated.

Synthesis of derivatives of pyrido[3,4-b]- and azepino[3,4-b]pyrrolo[2,3-d]pyrimidines from enamines of ?-oxo lactams

The reaction of enamines of some α-oxo lactams with 1,3-dimethyl- and 1,3-dibenzyl-4-hydrazinouracils gave the uracilyl-4-hydrazones of these lactams, the catalytic and thermal indolization of which yielded derivatives of pyrido[3,4-b]- and azepino[3,4-b]pyrrolo[2,3-d]pyrimidines. Some reactions of the latter were studied.

Synthesis and properties of 3-thiono derivatives of pyrido[2,3-e]-asym-triazine

2-Amino-3-hydrazinopyridine reacts with carbon disulfide to give 1,2,3,4-tetrahydropyrido[2,3-e]-asym-triazine-3-thione. The methylthio derivative obtained from it is oxidized to the sulfone, which undergoes exchange of the methylsulfonyl group for an amine residue in the cold. The methylthio derivative undergoes this sort of reaction only on heating, whereas in the cold it reacts with amines to give adducts that are unstable in solution and on heating.

Potential ambifunctionality of 2‐azidopyrido[1,2‐a] pyrimidin‐4‐one

Abstract2‐Azidopyrido[1,2‐a]pyrimidin‐4‐one can exit only in the azido form and undergoes cyclo‐addition reaction with 1,3‐dicarbonyl compounds to form 1,2,3‐triazole derivatives. Under the influence of bases or hydrochloric acid the carbonyl group is attacked with subsequent opening of the pyrimidine ring. This causes an immediate cyclization of the azide group to give a tetrazolo derivative. In a similar way a triazole ring can be formed from the appropriate hydrazino derivatives of pyrido[1,2‐a]pyrimidin‐4‐one.