Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)

By Alan R. Katritzky (Ed.)

(from preface)Volume fifty four of Advances in HeterocycUc Chemistry is a monograph quantity, i.e., it's dedicated to a unmarried topic, the aminomethylenemalo-nates.Aminomethylenemalonates are of serious value in heterocyclic synthesis and feature been utilized in the coaching of a truly large choice of heterocycles. The chemistry of this workforce of compounds has no longer been reviewed in additional than 50 years. the current remedy through Istvln Hermecz and co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. offers a complete overview.After an introductory part, paintings from the nineteenth century is in brief thought of and next sections talk about in flip the constitution and physicochemical houses of the aminomethylenemalonates, theirprepa-ration, and, within the biggest sections, the appliance of the aminomethylenemalonates to heterocyclic synthesis...

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Ph Ph The exothermic reactions of 3-aminopyrroles (62)and dialkyl alkoxymethylenemalonates in methanol or ethanol afforded 3-pyrrolylaminomethylenemalonates (63) in 67-85% yields (85JHC83, 85JHC729, 85JHC817). c MeSAs COOH HERMECZ et al. [Sec. 1 COOEt AlPhMe +EMHE COOEt -co2 SCHEME 14 4-Amino-(2-methylthio)thiazole-5-carboxylicacid was reacted with EMME in boiling toluene for 2 hr to give N-(2-methylthiothiazol-4yl)aminomethylenemalonate in 62% yield (84JHC1361) (Scheme 14). The reaction of 3-aminopyrazole and EMME at 100°C for 30 min gave 10% of pyrazolo[ 1,5-a]pyrimidinecarboxylate(64) and 25% of 3pyrazolylaminomethylenemalonate (70CB3252).

Minomethylenemalonates(60)in 60-74% yields (86SAP9289; 87FES787, 87JHC297). terf-Butyl 2-amino- I-benzyl-4,5-dimethyIpyrrole-3-carboxylate was reacted with dialkyl alkoxymethylenemalonates at 150- 160°C for 2-3 hr to afford 2-pyrrolylaminomethylenemalonates (61) in 38-65% yields (85JHC 1429). Ph Ph The exothermic reactions of 3-aminopyrroles (62)and dialkyl alkoxymethylenemalonates in methanol or ethanol afforded 3-pyrrolylaminomethylenemalonates (63) in 67-85% yields (85JHC83, 85JHC729, 85JHC817).

77JHC621) have been used. , triethylamine in methanol (68MIl)l. , 46JA1232, 46JA1268, 46JA1317; 5OJCS464, 50JOC1224; 58JCS828; 70CPB1385). The most frequently applied dialkyl alkoxymethylenemalonate is EMME. , 75JAP(K)49286; Sec. , 74MIPI ; 76ACH91). , 52LA48) are also sometimes used (Scheme 7). , 76JCS(P1)1331]. , 75IJC 1275)(Scheme 8). , 64JMC68, 64JMC487; 70CPB1385; 77GEP2612314; 78GEP2737542). Both 2-nitroaniline and N-methylaniline react less readily than aniline with EMME, but if these two groups are present at the same time (N-methyl-2-nitroaniline was used), no reaction occurred at all (59JCS2401) (Scheme 9).

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