4 carboxamide

The recently reported rearrangement (1581) of 2-allylamino-4-carboxamido-5-aminothiazoIes to 4-aminoimidazole-5-carboxamide in presence of sodium bicarbonate probably involves the electrophilic reactivity of C-2, which allows the ring opening. 

CbHORINE OXYGEN ACIDS AND SALTS - CbHOROUS ACID, CbHORITES, AND CbHORINE DIOXIDE] (Vol 5) [l-(2,6-Diethylphenyl)-imida2ole-5-carboxamide]... 

The aminolysis of esters of pyrimidine occurs normally to yield amides. The reagent is commonly alcoholic ammonia or alcoholic amine, usually at room temperature for 20-24 hours, but occasionally under refiux aqueous amine or even undiluted amine are used sometimes. The process is exemplified in the conversion of methyl pyrimidine-5-carboxylate (193 R = Me) or its 4-isomer by methanolic ammonia at 25 °C into the amide (196) or pyrimidine-4-carboxamide, respectively (60MI21300), and in the butylaminolysis of butyl ttracil-6-carboxylate (butyl orotate) by ethanolic butylamine to give A-butyluracil-5-carboxamide (187) (60JOC1950). Hydrazides are made similarly from esters with ethanolic hydrazine hydrate. 

The 4- and 5-amino-l,2,3-triazoles are diazotizable, e.g. the diazonium salt from 4-aminotriazole-5-carboxamide with potassium iodide gives the 4-iodo derivative, and that from 4-amino-l,5-diphenyltriazole gives 1,5-diphenyltriazole in ethanol (74AHC(16)33). 

H-Dibenz[6,/]azepine-5-carboxamide pharmacological properties, 7, 546 Dibenz[6,e]azepine-6,11-dione, 10-amino-reactions, 7, 526 Dibenz[6,e]azepinediones intramolecular nucleophilic substitution, 7, 516 synthesis, 7, 531 Dibenz[6,e]azepine-5,11-diones epoxides, 7, 515 reduction, 7, 525... 

Imidazole-5-carboxamide, 4-cyano-reduction, 5, 435 synthesis, 5, 461, 472 Imidazole-5-carboxamide, 4-mercapto-oxidation, 5, 445... 

Imidazole-5-carboxamide, l-methyl-4-nitro-mass spectra, 5, 359 Imidazole-4-carboxanilide, 1-methyl-synthesis, 5, 435 Imidazolecarboxylic acid, vinyl-polymers, 1, 281 Imidazole-2-carboxylic acid chlorination, 5, 398 mass spectra, 5, 360 synthesis, 5, 474... 

Pyrazolo-5-carboxamide, 4-hydroxy-3-/3-D-ribofuranosyl-occurrence, 5, 303 Pyrazolodiazepines synthesis, 5, 321... 

Pyrimidine-5-carboxamide, 4-amino-purine synthesis from, 5, 582 Pyrimidine-5-carboxamide, 4-amino- N- pheny synthesis, 3, 122 Pyrimidinecarboxamides Curtius degradation, 3, 82 dehydration, 3, 82 Hofmann degradation, 3, 82 hydrolysis, 3, 81 reactions, 3, 81 synthesis, 3, 127 Pyrimidinecarboxamides, thio-synthesis, 3, 128... 

Therapeutic Function Analgesic, Anticonvulsant Chemical Name 5H-dibenz[b,f] azepine-5-carboxamide Common Name 5-carbamyl iminostilbene Structural Formula ... 

AT-acetyltryptamines could be obtained via microwave-assisted transition-metal-catalyzed reactions on resin bound 3-[2-(acetylamino)ethyl]-2-iodo-lH-indole-5-carboxamide. While acceptable reaction conditions for the application of microwave irradiation have been identified for Stille heteroaryla-tion reactions, the related Suzuki protocol on the same substrate gave poor results, since at a constant power of 60 W, no full conversion (50-60%) of resin-bound 3-[2-(acetylamino)ethyl]-2-iodo-lH-indole-5-carboxamide could be obtained even when two consecutive cross-coupling reaction cycles (involving complete removal of reagents and by-products by washing off the resin) were used (Scheme 36). Also under conventional heating at 110 °C, and otherwise identical conditions, the Suzuki reactions proved to be difficult since two cross-coupling reaction cycles of 24 h had to be used to achieve full conversion. 

CN 6-mcthoxy-A -[[l-(2-propenyl)-2-pyrrolidinyI]methyl]-l/7-benzotriazole-5-carboxamide... 

Oro s experiment (Oro, 1960) was very simple he heated ammonium cyanide to 343 K and was able to detect adenine after a few days. Shortly afterwards, he showed that five molecules of HCN combined to give one of adenine (Oro, 1961). An intermediate, aminomalonitrile, can be converted to 4-aminoimidazole-5-carboxamide in two different ways (Sanchez et al., 1966a, b) (Fig. 4.4) ... 

The hydrolysis leads to 4-aminoimidazole-5-carboxamide, which under certain conditions can react with various partners (e.g., HCN, dicyan or formamidine) to give purines (i.e., adenine, guanine, hypoxanthine and diaminopurine). 

Fig. 4.5 The adenine synthesis can be varied to give other purine derivatives. Structures I-IX are those of I aminomalonitrile, II HCN tetramer, III aminoimidazole-carbonitrile, IV 4-aminoimidazole-5-carboxamide, V adenine, VI diaminopurine, VII xanthine, VIII guanine and IX hypo xanthine (Sanchez et al., 1966a)... 

A number of heteroaryl-fused 3-oxo-l,4-thiazepine-5-carboxamides, for example the indole-fused derivatives 133, have been accessed using a modification of the four-component Ugi condensation. In the case of 133, the starting point was the indolic acid 132. The yields of 133 were moderate to good (for example, R = -Pr, R2= EtO-(CH2)3, 66%) <06JOC2811>. 

The 1,3-dipolar cycloaddition of a variety of aromatic and aliphatic nitrile oxides to 2.5-/ra//.v-2.5-diphenylpyrrolidine-derived acrylamide and cinnamamide 399, efficiently affords the corresponding 4,5-dihydroisoxazole-5-carboxamides 400 in highly regio- and stereoselectivity (Scheme 1.47). Acid hydrolysis of these products affords enantiopure 4,5-dihydroisoxazole-5-carboxylic acids 401 (443). 

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