Unusual reactions of 4,6-dichloro-5-nitropyrimidine with C-nucleophiles

Azev, Yuri A.; Duelcks, Thomas; Lork, Enno; Gabel, Detlef

doi:10.1070/mc2005v015n05abeh002156

Mendeleev Communications

2005

DOI: 10.1070/mc2005v015n05abeh002156

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Unusual reactions of 4,6-dichloro-5-nitropyrimidine with C-nucleophiles

Yuri A. Azev¹,

Thomas Duelcks

Enno Lork

et al.

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Cited by 3 publications

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“…Heating VIII and a three-fold molar excess of 2-methylindole for 1 h in refluxing ethanol produced the halo-substitution product 4-(2-methylindol-3-yl)quinazoline (X) and the known tris(2-methylindol-3-yl)methane (XI) [10].…”

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Reactions of quinazoline and its 4-oxo- and 4-chloro-substituted derivatives with nucleophiles

2011

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Reaction of quinazoline (I) with 2-methylindole, pyrogallol, and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to the formation of C-4 adducts II, III, and V. Adduct IV was obtained by heating I with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-5-one reacts with I without acid catalysis with the formation of dipyrazolylmethane VI. 4-Chloroquinazoline VIII reacts with 1-phenyl-3-methylpyrazol-5-one to yield 4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl)quinazoline IX and dipyrazolylmethane VI. Heating VIII with 2-methylindole leads to formation of 4-(2-methylindol-3-yl)quinazoline X and tris(2-methylindol-3-yl)methane XI. The proposed structures were confirmed by NMR spectral data.

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Reactions of quinazoline and its 4-oxo- and 4-chloro-substituted derivatives with nucleophiles

2011

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Unusual Reactions of 4,6‐Dichloro‐5‐nitropyrimidine with C‐Nucleophiles.

Azev¹,

Duelcks

Lork

et al. 2005

ChemInform

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Interaction of title compound (I) with pyrazolone (II) yields the dipyrazolylmethane (III) as major product besides the two-halogen replacement product (IV). The unusually easy reaction of (I) with indole (V) is explained by evolving hydrogen chloride, which catalyzes indole addition and disintegration of the intermediate yielding salt (VI). The tris(indolyl)methane (VII) results from addition of the third methylindole molecule to diindolylmethane (VI). Replacement of one indolyl moiety occurs in the reaction course of salt (VI) with dimethylbarbituric acid (VIII). The latter compound reacts with dimethylsulfoxide (X) to betaine (XI) in the presence of (I) as dehydrating reagent.-(AZEV*, Y. A.; DUELCKS, T.; LORK, E.; GABEL, D.; Mendeleev Commun. 2005, 5, 193-196; Ural State Tech. Univ., Ekaterinburg 620002, Russia; Eng.) -H. Hoennerscheid 03-043

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Transformations of 6,7-difluoroquinoxaline with Indoles: Synthesis of Indole-Substituted 6,7-difluoroquinoxalines and Tris(indol-3-yl)methane Derivatives

et al. 2017

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Unusual reactions of 4,6-dichloro-5-nitropyrimidine with C-nucleophiles

Cited by 3 publications

References 8 publications

Reactions of quinazoline and its 4-oxo- and 4-chloro-substituted derivatives with nucleophiles

Reactions of quinazoline and its 4-oxo- and 4-chloro-substituted derivatives with nucleophiles

Unusual Reactions of 4,6‐Dichloro‐5‐nitropyrimidine with C‐Nucleophiles.

Transformations of 6,7-difluoroquinoxaline with Indoles: Synthesis of Indole-Substituted 6,7-difluoroquinoxalines and Tris(indol-3-yl)methane Derivatives

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