5098-11-3Relevant articles and documents
SYNTHESIS AND PROPERTIES OF ANALOGS OF 5(OR 4)-AMINOIMIDAZOLE-4(OR 5)-CARBOXAMIDE (AICA) AND PURINES. 12. INVESTIGATION OF THE INTERACTION OF 4-CHLOROIMIDAZO-1,2,3-TRIAZINE WITH NUCLEOPHILES
Mokrushin, V. S.,Pospelova, T. A.,Shafran, Yu. M.
, p. 1231 - 1234 (1983)
The reactions of 4-chloroimidazo-1,2,3-triazine with a number of nucleophilic reagents have been studied.Either replacement of the chlorine atom in position 4 of the 1,2,3-triazine ring or opening of the triazine ring with the formation of products of the interaction of the intermediate 5-diazoimidazole-4-carbonitrile with these nucleophiles occurs, depending on the nucleophilicity of the reagent.
Guanidine: Studies on the reaction with ethyl N-(2-amino-1,2-dicyanovinyl) formimidate
De Assuncao, Luisa R.,Marinho, Elina R.,Proenca, Fernanda P.
experimental part, p. 82 - 91 (2010/08/22)
Formimidate 1 was reacted with guanidinium chloride, at room temperature, in the presence of sodium ethoxide and in dilute THF solution, leading to pyrimidine 10 by an unusual intramolecular cyclization process. A different reaction mechanism operated when imidate 1 was combined with guanidinium acetate in nitromethane under reflux. Structure 14 is tentatively assigned to this new product.
METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)IMIDATE, METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)FORMAMIDINE, AND METHOD FOR PRODUCTION OF AMINOIMIDAZOLE DERIVATIVE
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Page/Page column 15, (2010/01/07)
A method for producing N-(2-amino-1,2-dicyanovinyl)imidates represented by the following formula (1-III) under low temperature conditions within a short period of time in high yield is provided. In addition, a method for producing N-(2-amino-1,2-dicyanovinyl)formamidine represented by the following formula (2-II) which is suitably applicable to a cyclization reaction for producing AICN, AICA or the like and which enhances yield of the cyclization reaction is provided. In addition, a method for producing aminoimidazole derivatives represented by the following formula (3-V) in high yield by using diaminomaleonitrile as a starting material is provided.
Treatment of bacterial induced diseases using DNA methyl transferase inhibitors
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Page/Page column 29, (2008/06/13)
Methods for treating and/or preventing disease conditions caused or induced or aggravated by microbes, especially bacteria, by inhibiting DNA methyltransferase activity, such as by administering to an animal a DNA methyltransferase inhibitor, are disclosed, along with methods of reducing or ablating virulence in bacteria by inhibiting DNA methyltransferase activity.
DNA Methyltransferase inhibitors
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Page 24, (2008/06/13)
A compound of the formula or a pharmaceutically acceptable salt thereof,whereinR1, R2, and R3 are the same or different and are independently hydrogen, lower alkyl, aryl or substituted aryl, lower alkoxy, lower alkoxyalkyl, or cycloalkyl or cycloalkyl alkoxy, where each cycloalkyl group has from 3-7 members, where up to two of the cycloalkyl members are optionally hetero atoms selected from oxygen and nitrogen, and where any member of the alkyl, aryl or cycloalkyl group is optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, andwhereR3 can be ribose, deoxyribose or phosphorylated derivatives thereof,whereinR1, R2, and R3 are not all hydrogen andwhereinwhen R3 is ribose, deoxyribose or phosphorylated derivatives thereof, one of R1 or R2 is not hydrogen.
Synthesis of 5-Amino-4-(cyanoformimidoyl)-1H-imidazole: a Reactive Intermediate for the Synthesis of 6-Carbamoyl-1,2-dihydropurines and 6-Carbamoylpurines
Alves, M. Jose,Booth, Brian L.,Proenc, M. Fernanda J. R. P.
, p. 1705 - 1712 (2007/10/02)
5-Amino-4-(cyanoformimidoyl)-1H-imidazole (3) has been prepared in good yield by the basecatalysed cyclisation of (Z)-N-(2-amino-1,2-dicyanovinyl)formamidine.Compound (3) reacts with ketones, R1COR2 to give 2,2-disubstituted-6-carbamoyl-1,2-dihydropurines as the major products, together with minor amounts of compounds believed to be novel 7-amino-1-carbamoyl-3,3-disubstituted 3H-imidazoimidazole derivatives, which have been isolated when R1= R2= Et, Bu, and PhCH2; when R1= R2= Ph the only product isolated is tentatively assigned the imidazoimidazole structure.In the reaction with acetylacetone the 1,2-dihydropurine intermediate is unstable and loses acetone to give 2-methyl-6-carbamoylpurine.The aldehydes RCHO also react readily with (3) at room temperature to give the corresponding 6-carbamoyl-1,2-dihydropurine derivatives, which can be isolated when R= Me or Et; these oxidise in solution to afford the corresponding 6-carbamoylpurines.
SYNTHESIS AND PROPERTIES OF ANALOGS OF 5(4)-AMINOIMIDAZOLE-4(5)-CARBOXAMIDE AND PURINES. 15. RING OPENING IN IMIDAZO-1,2,3-TRIAZINES
Usova, V. K.,Selezneva, I. S.,Pospelova, T. A.,Mokrushin V. S.
, p. 1045 - 1047 (2007/10/02)
It has been shown that 4-methylthio-, ethoxy-, and methoxyimidazotriazines and imidazotriazin-4-ones, unlike benzo-1,2,3-triazines, do not display cryptodiazonium behavior.A novel type of fission of the triazine ring to give esters and thioesters of 5-aminoimidazole-4-carboxylic acid is described.
Rearrangements in Heterocyclic Synthesis: A Novel Translocation of an (N-Amino-N-methylamino)methylene Group from a Heterocyclic N-Amino-N-methylformamidine Side Chain to the Vinylogous Nitrile Function
Hosmane, Ramachandra S.,Lim, Benjamin B.,Burnett, Friedrich N.
, p. 382 - 386 (2007/10/02)
Reaction of the imidate 1-benzyl-4-cyano-5imidazole (5) with an equivalent of hydrazine provided 1-amino-9-benzyl-6-iminopurine (6), which, upon treatment which excess hydrazine, rearranged to 9-benzyl-6-hydrazinopurine (7).Reaction of 5 with methylhydrazine gave N-amino-N-methyl-N'-(1-benzyl-4-cyanoimidazol-5-yl)formamidine (8b).Thermolysis of 8b in refluxing toluene-methanol, catalyzed by trifluoroacetic acid, provided an equimolar mixture of 5-amino-1-benzyl-4-cyanoimidazole (9) and 3-(5-amino-1-benzylimidazol-4-yl)-1-methyl-1,2,4-triazole (10).Compound 9 was recycled to 8b via 5.The structure of 10 was established by spectral data coupled with an unequivocal synthesis.The conversion 8b to 10 represents a novel "translocative" rearrangement involoving the transfer of an NH2N(Me)CH= group from the imidazole 5-position to the nitrile function at position 4.Successful application of the rearrangement to the analogous pyrazole system is demonstrated.The rearrangement carries useful practical implications in the synthesis of the otherwise not easily accessible heterocycles of potential biological and medicinal significance.
Synthesis of 5 (3,3 disubstituted 1 triazenyl)imidazole 4 carbonitriles
Shealy,O'Dell
, p. 954 - 956 (2007/10/05)
The 3,3 dimethyl 3 n butyl 3 methyl, 3 (2 hydroxyethyl) 3 methyl, 3,3 bis (2 fluoroethyl), and 3,3 bis (2 chloroethyl) 1 triazenyl derivatives of imidazole 4 carbonitrile were prepared from 5 diazoimidazole 4 carbonitrile, a stable compound which produced
