- New synthesis of 1,5-disubstituted imidazoles
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A new synthesis of 1-alkylimidazole-5-carbaldehydes starting from [3- (dimethylamino)-2-azaprop-2-enylidene]dimethylammonium chloride and alkyl N- alkylglycinate is described.
- Kirchlechner,Casutt,Heywang,Schwarz
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- 2-(1H-INDOLE-3-CARBONYL)-THIAZOLE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS
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2-(1H-lndole-3-carbonyl)-thiazole-4-carboxamide derivatives and the corresponding imidazole, oxazole and thiophene derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders. The present description discloses the synthesis and characterisation of exemplary compounds as well as pharmacological data thereof (e.g. pages 27 to 32 and 59 to 219; examples 1 to 8; compounds 1-1 to 1-97; tables 1-a, 2 and 3).
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Paragraph 00162; 00198
(2021/06/26)
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- Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase
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Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.
- Collman, James P.,Yan, Yi-Long,Lei, Jianping,Dinolfo, Peter H.
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p. 923 - 926
(2007/10/03)
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- Process for the preparation of 5-membered nitrogen containing heteroaromatics
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Compounds of the formula I STR1 in which A and X1 have the meaning given in patent claim 1 can be prepared in a simple manner, in a one-pot process and in high yields.
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- Preparation of 1-alkylimidazoles
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Process for the preparation of 1-alkylimidazoles of the general formula (I) STR1 where R1 is alkyl, R2 and R3 are hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, R4 is carboxy, alkoxycarbonyl R5 OCC--, carbamoyl, or cyano, and R5 is an alkyl of from 1 to 8 carbon atoms--by the reaction of imidazoles of the general formula (II) STR2 with dialkyl sulfates of the general formula (III) at elevated temperatures in the presence of a carboxylic acid or anhydride or of both acid and anhydride.
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- Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate
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Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented.One proceeds from sarcosine via ring closure, bromination, and desulfurization.The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange.The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13).Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16).Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18).Subsequent dibromination gives the completely substituted imidazole 8.The primary purification in this sequence is fractional sublimation of 18 after the esterification step.An overall yield of 26percent is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.
- O'Connell, John F.,Parquette, Jonathan,Yelle, William E.,Wang, Wilhelm,Rapoport, Henry
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p. 767 - 771
(2007/10/02)
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- Selective Decarboxylation of 1-Methyl-4,5-imidazoledicarboxylic Acid
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The selective decarboxylation of 1-methyl-4,5-imidazoledicarboxylic acid was carried out in various solvents. 1-Methyl-5-imidazolecarboxylic acid was obtained by heating in acetic or propionic anhydride, whereas 1-methyl-4-imidazolecarboxylic acid was obtained in N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone or by pyrolysis.The reaction mechanism is discussed.
- Takahashi, Kazuyuki,Mitsuhashi, Keiryo
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p. 557 - 558
(2007/10/02)
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