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1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with phenyl azide gave a regioselective product, 1-phenyl-4-trimethylstannyl-1,2,3-triazole. On the other hand, the reaction of trimethylstannyl-1-hexyne, -phenylacetylene, and -trimethylsilylacetylene with the azide yielded a mixture of the corresponding 4- and 5-trimethylstannyl-1-phenyl-1,2,3-triazoles. Detrimethylstannylation, iodination, benzoylation, and palladium-catalyzed phenylation of 4-trimethylstannyl- and 4,5-bis(trimethylstannyl)-1-phenyl-1,2,3-triazoles were also described

Methyl 2-(nitrogen-heteroaryl)propanoates were synthesized by the palladium-catalyzed reaction of heteroaryl halides with (E)-1-methoxy-1-trimethylsiloxypropene

1,3-Dioxep-5-ene was arylated by using Heck reaction, and the arylated 1,3-dioxep-4-ene derivatives were easily converted into 4-arylbutyrolactones, intermediates for the synthesis of natural products and biological active compounds

2-Arylindoles were synthesized by the palladium-catalyzed reaction of aryl halides with 2-indolylzinc derivatives which were derived from the lithio derivatives

1,3-Dipolar cycloaddition reaction of diazomethane and ethyl diazoacetate with tributylstannyl-acetylenes occurred regioselectively to afford the corresponding 3(5)-tributylstannylpyrazoles. The cycloaddition reaction of 3-phenylsydnone with the stannylacetylenes proceeded also regioselectively, and 3-tributylstannyl-1-phenylpyrazoles were isolated. 4-Tributylstannyl- and 5-tributylstannyl-1-phenylpyrazole were prepared by the stannylation of 4-lithio- and 5-lithio-1-phenylpyrazoles with tributylstannyl chloride. Iodination, benzoylation, and phenylation of the stannylpyrazoles were examined

Four kinds of 1 H-pyrrolopyridines having no substituent were simply and easily synthesized by the palladium-catalyzed reaction of easily available nitropyridine derivatives with (Z)-1 -ethoxy-2-tributylstannylethene as a key reaction

The synthesis of methyl 6-alkylamino-3-pyridazinecarboxylates (4a-c) was accomplished by the following reaction sequence. On treatment of methyl 6-chloro-3-pyridazinecarboxylate (1) with methanolic ammonia, 6-chloro-3-pyridazinecarboxamide (5) was precipitated almost quantitatively, which reacted with primary alkylamines to give the corresponding 6-alkylamino-3-pyridazinecarboxamide (6a-c). These products were smoothly converted into the methyl esters (4a-c) by treatment with methanol in the presence of boron trifluoride etherate. The reaction of 1 with butylamine in THF gave a complicated mixture in which N-butyl-6-chloro-3-pyridazinecarboxamide(2), N-butyl-6-butylamino-3-pyridazinecarboxamide(3), 4b, and 1 were involved

Inverse electron-demand Diels-Alder reaction of 3,6-disubstituted 1,2,4,5-tetrazines with tributylstannylacetylenes containing a substituent gave 4-(tributylstannyl)pyridazines. Particularly, dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate gave 4-(tributylstannyl)pyridazines in good yields. Substitution reaction of 3,6-diphenyl-4-(tributylstannyl)pyridazine was also described

Nucleophilic addition-elimination reactions of 2-methylsulfonyl-1,3-azoles with active methylene compounds were investigated in order to compare the reactivity of substrates. The order of oxasole > thiazole >> N-methylimidazole in the reactivity was exhibited clearly. Furthermore, in oxazole and thiazole series, the predominant reactivity of the 2-position over the 4- and 5-positions was indicated on the reaction with the carbanions generated from active methylene compounds

Homolytic chlorination of 5,6-dimethyl-as-triazine with Cl 2 gave 6-dichloromethyl-5-trichloromethyl-as-triazine (I) selectively. Structural determination of I by chemical method and synthesis of 5-amino-6-formyl-as-triazine derivatives are described.

The reaction of 3-bromopyridine with phenylacetonitrile in the presence of NaH in THF gave a simple substitution product, α-phenyl-3-pyridineacetonitrile, whereas the reaction of 5-bromopyrimidine with phenylacetonitrile under similar conditions gave a ring-transformation product, 2-amino-5-bromo-3-phenylpyridine. 3-bromoquinoline and 4-bromoisoquinoline underwent the former type reaction, while 3-bromo- and 3-chloroisoquinolines were converted into 2-amino-3-phenyl-1-naphthalencarbonitrile according to the latter type reaction

The syntheses and reactions of pyrimidines N-oxides are reviewed. Pyrimidines having alkyl, aryl, and alkoxyl groups are convertible to their mono-N-oxides by N-oxidation with an organic peroxy acid. The position of the N-oxide group can be elucidated by physical methods. Pyrimidine N-oxides are highly reactive to various nucleophilic reagents owing to their π-deficient character. The reactivity of a methyl group enhanced by introducing an N-oxide group and the characteristic ring-cleavage of N-oxides are also described

Title reaction is well prompted by the catalytic action of dichlorobis(triphenylphosphine)palladium in dimethylformamide in the presence of tetraethylammonium chloride to give (Z)-1-ethoxy-2-(4-substituted phenyl)ethene. The method is also useful for the introduction of a 2-ethoxyethenyl moiety into heteroaromatic rings such as pyridine, thiophene, indole

The monomethoxyl derivatives of various π-electron-deficient N-heteroaromatics reacted with phenylacetonitrile in tetrahydrofuran in the presence of sodium hydride to give α-phenyl-N-heteroareneacetonitriles in the yields ranging from 45 to 78 %. On the contrary, the reaction of these methoxyl derivatives with ethyl cyanoacetate or malononitrile under similar conditions was restricted within narrow limits. The synthesis of benzoyl-N-heteroaromatics by the air-oxidation of α-phenyl-N-heteroareneacetonitriles was described additionally

This type ring-transformation(intramolecular reverse electron-demand Diels-Alder reaction) was applicable to the corresponding 3,5-diphenyl-1,2,4-triazine-6-carboxylic acid esters. According to the similar manner, benzofuro[2,3-b]pyridines, benzofuro[2,3-c]pyridines, and benzofuro[2,3-d]pyridines were synthesized in satisfactory yields. The Diels-Alder reaction of 3-(2-phenylethynylphenoxy)-1,2,4-benzotriazine afforded 11-phenylbenzofuro[2,3-b]quinoline.

Synthese d'indole, indolecarboxylate-4 d'ethyle et dimethyl-5,7 pyrrolo [2,3-c] pyridine respectivement a partir de bromo-1 nitro-2 benzene, bromo-2 nitro-3 benzoate d'ethyle et chloro-4 dimethyl-2,6 nitro-3 pyridine par l'intermediaire de l'action d'HCl dans l'ethanol sur le diethylacetal de l'amino-2 benzeneacetaldehyde et composes correspondants

Obtention des derives phenyl-5 puis diphenyl-5,6 puis triaryl-3,5,6 (la derniere addition se faisant avec le bromure de p-methoxyphenylmagnesium)

Synthese par reaction de diiodo-4,6 methyl-2 pyrimidine avec l'iodure de trimethylsilyl-5 pentyne-4yl zinc en presence de complexe de palladium

Article de synthese traitant de la synthese catalysee par le palladium complexe ou Pd II (OAc) 2 d'intermediaires heterocycliques tels que des indoles, quinoleines, isoquinoleines et d'autres heterocycles oxygene- ou soufre azote

Synthese d'oxydes-2 de R-3 isoquinoleines et des derives dimethoxy-6,7 u partir de bromo-2 benzaldehyde ou de son derive dimethoxy-4,5 et de R acetylene