2005
DOI: 10.1002/ejoc.200500522
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Synthesis of Annelated Azaheterocycles Containing a 5‐Carbamoylpyrazin‐3‐one Fragment by a Modification of the Four‐Component Ugi Reaction

Abstract: A convenient synthesis of novel imidazole-and pyrrole-fused 1-oxo-1,2,3,4-tetrahydropyrazine heterocyclic structures by a novel modification of the four-component Ugi condensation is described. The usefulness and versatility of the developed approach for the synthesis of variously substituted com-

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Cited by 13 publications
(3 citation statements)
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“…The parent heterocycle I was synthesized in 1957 by the reductive cyclization of 3-nitro-2-thienylpyruvic acid, followed by decarboxylation of the product, namely, thieno[3,2- b ]pyrrole-5-carboxylic acid, and also by the reduction of 2 H ,3 H -thieno[3,2- b ]pyrrol-3-one obtained via cyclization of pyrrole-3-thioacetic acid . The general synthetic approach to the substituted alkyl thieno[3,2- b ]pyrrole-5-carboxylates includes transformation of compounds II into numerous derivatives III under treatment of different reagents. For example, the reported works describe synthesis of alkyl thieno[3,2- b ]pyrrole-5-carboxylates III with the following substituents: 2-formyl, , 2-acetyl, 2-bromo, 2,6-dibromo, 2,3,6-tribromo, 2-nitro, 2,6-dinitro, 3-formyl, 4-benzyl, 4-(2-nitrobenzyl), , 6-dimethylaminomethyl, 6-(1-piperidinylmethyl), 6-cyanomethyl, 6-formyl, , 2-methyl-3-acyl, 2-methyl-3,6-diacyl, , 2-methyl-4-(2-oxopropyl), and 2-methyl-4-(2-oxo-2-phenylethyl) . Some of the mentioned esters were then hydrolyzed to the corresponding acids, which usually served as convenient starting materials in subsequent tran...…”
Section: Introductionmentioning
confidence: 99%
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“…The parent heterocycle I was synthesized in 1957 by the reductive cyclization of 3-nitro-2-thienylpyruvic acid, followed by decarboxylation of the product, namely, thieno[3,2- b ]pyrrole-5-carboxylic acid, and also by the reduction of 2 H ,3 H -thieno[3,2- b ]pyrrol-3-one obtained via cyclization of pyrrole-3-thioacetic acid . The general synthetic approach to the substituted alkyl thieno[3,2- b ]pyrrole-5-carboxylates includes transformation of compounds II into numerous derivatives III under treatment of different reagents. For example, the reported works describe synthesis of alkyl thieno[3,2- b ]pyrrole-5-carboxylates III with the following substituents: 2-formyl, , 2-acetyl, 2-bromo, 2,6-dibromo, 2,3,6-tribromo, 2-nitro, 2,6-dinitro, 3-formyl, 4-benzyl, 4-(2-nitrobenzyl), , 6-dimethylaminomethyl, 6-(1-piperidinylmethyl), 6-cyanomethyl, 6-formyl, , 2-methyl-3-acyl, 2-methyl-3,6-diacyl, , 2-methyl-4-(2-oxopropyl), and 2-methyl-4-(2-oxo-2-phenylethyl) . Some of the mentioned esters were then hydrolyzed to the corresponding acids, which usually served as convenient starting materials in subsequent tran...…”
Section: Introductionmentioning
confidence: 99%
“…Syntheses of several annulated heterocycles possessing the 4 H -thieno[3,2- b ]pyrrole moiety have been previously described, for example, thieno[2,3- b ]indolizine IV , 5,6,7,8-tetrahydro-4 H -thieno[3‘,2‘:2,3]pyrrolo[4,5- c ]pyridine V , 8-oxo-5,6,7,8-tetrahydrothieno[2‘,3‘:4,5]pyrrolo[1,2- a ]pyrazine VI , 3 H ,4 H ,5 H -thieno[3‘,2‘:2,3]pyridazin-4-ones VII , , and 5-oxo-6,11-dihydro-5 H -benzo[e]thieno[2‘,3‘:4,5]pyrrolo[1,2- a ] 1,4 diazepine VIII . Among the synthesized compounds containing the thieno[3,2- b ]pyrrole moiety, several physiologically active agents were described.…”
Section: Introductionmentioning
confidence: 99%
“…Such examples are cyclization of imidazolecarboxamides, 5 ring opening of theophyllin-7-acetic acid with subsequent cyclization, 6 cyclization of chiral hydroxyethylaminocarbonyl substituted imidazole derivatives, 7 and a modification of the Ugi reaction with 4-methoxycarbonyl-1-(2-oxopropyl)-1H-imidazole-5-carboxylic acid. 8 Furthermore, some fused imidazo [1,5-a]pyrazines have also been investigated. For example, such compound is the 5,10-methylenetetrahydrofolate, a very important coenzyme.…”
mentioning
confidence: 99%