Synthesis of 1-substituted-2,3,4,9-tetrahydro-(2-oxopropyl)-1H-pyrido [3,4-b] indoles and their base-catalyzed rearrangements to N- [2-[2-(1-alkyl-3-oxobutenyl)-1H-indol-3-yl] ethyl]acetamides

The condensation of 1H-indole-3-ethanamides, 1 , with 2,4-pentanediones, 2 , gave enamines 3 . Acid catalyzed ring closure of 3 gave 1-(1-substituted-2,3,4,9-tetrahydro- (2-oxopropyl) -1H-pyrido [3,4-b] indoles 4 . Subsequent N-acetylation yielded 5 which sequentially produced 2,3-disubstituted indoles 6 and 7 resulting from C? N bond cleavage after treatment with sodium alkoxide in ethanol. Controlled catalytic hydrogenation of the latter gave saturated derivatives 8 and 9 .     

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indoles. II. Reversible transformation of 1-alkyl-2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)cyclohexanol into 1-alkylidene-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles

Treatment of 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1-methylcyclohexanol ( 2a ) with acetic anhydride or methyl isocyanate gave 2-acetyl-2,3,4,9-tetrahydro-1-(6-oxoheptylidene)-1H-pyrido[3,4-b]indole ( 3 ) or 1,3,4,9-tetrahydro-N-methyl-1-(6-oxoheptylidene)-2H-pyrido[3,4-b]indole-2-carboxamide ( 4 ), respectively. Simpler analogues, 1-alkyl-4,9-dihydro-3H-pyrido[3,4-b]indoles, 7 , subjected to identical reaction conditions, gave 2-acetyl-1-alkylidene-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles 8 and 1,3,4,9-tetrahydro-N-methyl-1-alkyli-dene-2H-pyrido[3,4-b]indole-2-carboxamides 9 , respectively. A limited lanthanide shift reagent study to determine stereochemical assignments was also performed.     

Three-component,four-centered,one-pot synthesis of 1-(arylethynyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole derivatives

An efficient three component, four-centered A3 coupling strategy has been developed for the synthesis of a novel series of 1-arylethynyl-tetrahydro-β-carboline derivatives in good yields with high selectivity. This method is also useful for the preparation of 1-arylethynyl tetrahydroisoquinolines, which can be used for the synthesis of biologically active molecules such as homolaudanosine, dysoxyline, methopoline and almorexant. The use of a readily available ZnCl₂/Et₃N reagent system makes this method simple, convenient and practical.     

1,1-Disubstituted-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indolecarboxylic acid esters and ketones. The base catalyzed transformation of 1-(2′,3′,4′,9′-tetrahydrospiro[cyclohexane-1,1′-[1H]pyrido[3,4-b]indol]-2-yl)alkanones into 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1 -alkylcyclohexanols

Condensation of 1H-indole-3-ethanamines 1 with cyclic β-keto esters 2 under azeotropic conditions followed by acid-catalyzed ring closure of the resulting enamines 3 gave 2′,3′,4′,9′-tetrahydrospiro[piperidine-3,1′,-[1H]pyrido[3,4-b]indole] -4-carboxylic acid alkyl esters 4 . Condensation of 1 with 2-acylcycloalkanones 8 gave two types of enamines, 10 and 11 , respectively. Enamines 10 on treatment with acid gave 1-(2′,3′,4′,9′-tetrahydro-3H-pyrido[3,4-b]indol-1-yl)-1-alkylcyclohexanols 17 . Compounds 17 were further dehydrated to give cycloalkane derivatives 19.     

Synthesis and Structure of 5-Aryl-4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,3-diones

Russian Journal of General Chemistry - The reactions of tryptamine with aromatic aldehyde and methyl benzoylpyruvate at room temperature leads to the formation of...     

Synthesis,Crystal Structure and Antitumor Activities of Ethyl(R)-2-(Biphenyl-4-carbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate

The title compound,ethyl(R)-2-(biphenyl-4-carbonyl)-2,3,4,9-tetrahydro-1H-pyri do-[3,4-b]indole-1-carboxylate(C_(27)H_(24)N_2O_3) has been synthesized,and its structure was charac-terized by ~1H-NMR,~(13)C-NMR,ESI-MS and single-crystal X-ray diffraction.It crystallizes in the orthorhombic system,space group Pbca with a = 16.9950(8),b = 9.5445(4),c = 28.3188(3) ?,V = 4593.6(3) ?~3,Z = 8,T = 294.64(10) K,μ(MoKα) = 0.08 mm~(-1),Dc = 1.228 g/cm~3,F(000) = 1792 and GOOF = 1.036.11836 reflections were measured(7.04≤2θ≤52.04°),and 4506 were unique(R_(int)= 0.0393,R_(sigma )= 0.0546) and used in all calculations.The final R = 0.0576(I 2σ(I)) and wR = 0.1563(all data).The preliminary biological tests show that the title compound has a good antitumor activity against Hela in vitro with the IC_(50) value of 4.71 μmol/L.     

Synthesis and structural characterization of 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride

In the course of studies on hybrid antibacterials incorporating 2-aryl-5-nitro-1H-indole moieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurally characterized. This pyridinium chloride salt crystallized in the monoclinic space group P2(1)/c with the following unit cell dimensions: a 10.274(3) ?, b 13.101(4) ?, c 13.439(4) ?, b 107.702(7)°, V 1723.2(9) ?3, Z (f.u.) = 4; R1 = 0.048, and wR2 = 0.13. Of interest in the single crystal X-ray structure is the (intramolecular) disposition of the pyridinium plane over the indole heterocyclic residue [interplanar dihedral angle 17.91(4)°].     

Facile and efficient synthesis of 1-[2-(6,7-dimethyl-3,4-dihydronaphthalen-2-yl)ethyl]pyrrolidine hydrochloride

An efficient and facile procedure for the preparation of 1-[2-(6,7-dimethyl-3,4-dihydronaphthalen-2-yl)ethyl]pyrrolidine hydrochloride from 6,7-dimethyl-1,2,3,4-tetrahydronaphtalen-1-one in four steps is proposed. It includes one-step synthesis of 1-(6,7-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid as key intermediate and subsequent transformations of functional groups therein. Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 3, pp. 449–453. The text was submitted by the authors in English.     

Synthesis of substituted 1-[2-(adamantan-1-yl)ethyl]piperidines

Quaternary 1-[2-(adamantan-1-yl)ethyl]pyridinium bromides were reduced with sodium tetrahydridoborate in ethanol, and hydroarylation of the resulting 1-[2-(adamantan-1-yl)ethyl]-1,2,3,6-tetrahydropyridines with benzene in trifluoromethanesulfonic acid afforded phenylpiperidines with preferentially equatorial orientation of the phenyl substituent.     

Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones

Russian Journal of General Chemistry - 1-[2-(1H-indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrole-2(5H)-ones were synthesized by the short heating of a mixture of tryptamine, aromatic...     

Condensation reaction of 3,4-dibenzoyl-1-methyl-2,5-diphenylpyrrole and -1-phenylpyrazole with methylamine derivatives affording pyrrolo [3,4-c]pyridine and 2H-pyrazolo[3,4-c]- and [4,3-c]pyridines

The reaction of 3,4-dibenzoyl-1-methyl-2,5-diphenylpyrrole ( 1 ) and -1-phenylpyrazole ( 2 ) with methylamines ( 3a-c ) afforded pyrrolo[3,4-c]pyridine ( 4 ), and isomeric 2H-pyrazolo[3,4-c]pyridines ( 5a-c ) and [4,3-c]pyridines ( 6a-c ), respectively.     

Synthesis,Crystal Structure and Antitumor Activities of N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline

The title compound, N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline(C16H15N3O2, Mr = 281.31), has been synthesized by the multicomponent reaction of milder Ullmann, and its structure was characterized by 1H NMR, 13 C NMR, IR, H RMS(ESI) and single-crystal X-ray diffraction. It crystallizes in monoclinic, space group I2/c with a = 15.0212(10), b = 9.4911(6), c = 20.3075(13) A, β = 100.776(7)o, V = 2844.1(3)A3, Z = 8, Dc = 1.314 g/cm3, F(000) = 1184.0, μ = 0.089 mm-1, the final R = 0.0574 and w R = 0.1688 for 1701 observed reflections(I 2σ(I)). X-ray analysis indicates three major N(2)–H(2)···O(2), C(13)–H(13)···O(2), N(2)–H(2)···N(3) hydrogen bonds and π-π stacking interactions in the crystal structure. The preliminary biological test shows that the title compound has a good antitumor activity against A549 in vitro with the IC50 value of 35 μmol/L.     

N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺及其类似物的合成

N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺是最近从海洋细菌中分离得到的一种新型的天然杀藻剂, 以D-丙氨酸为原料合成了该化合物, 并用类似的方法首次合成了它的类似物2, 3和4. 其关键步骤为通过将取代的4-噻唑甲酸制成混酐与色胺连接的偶联反应. 各中间体都通过¹H NMR和¹³C NMR得到证实. 最终产品通过¹H NMR, ¹³C NMR和HRMS证实, 与文献所报道相一致.     

Synthesis of 1-acetyl-2-silyoxycycloheptane derivatives via highly stereoselective formal [5+2] cycloaddition reaction

A stereoselective [5+2] cycloaddition reaction using a new five-carbon unit, that has a dicobalt acetylene complex moiety and an enol silyl ether moiety, was developed. In the presence of a Lewis acid, the five-carbon unit reacted with an enol triisopropylsilyl ether to give a 1-acetyl-2-silyoxycycloheptane derivative, in which the three contiguous substituents on the seven-membered ring arrange cis to each other.