Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.) PDF
By Alan R. Katritzky (Ed.)
(from preface)Volume fifty four of Advances in HeterocycUc Chemistry is a monograph quantity, i.e., it really is dedicated to a unmarried topic, the aminomethylenemalo-nates.Aminomethylenemalonates are of serious value in heterocyclic synthesis and feature been utilized in the education of a truly wide array of heterocycles. The chemistry of this crew of compounds has no longer been reviewed in additional than 50 years. the current remedy by way of Istvln Hermecz and associates, Geza Kareszturi and Lelle Vasv^ri-Debreczy. presents a entire overview.After an introductory part, paintings from the nineteenth century is in short thought of and next sections talk about in flip the constitution and physicochemical homes of the aminomethylenemalonates, theirprepa-ration, and, within the biggest sections, the applying of the aminomethylenemalonates to heterocyclic synthesis...
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Additional info for Advances in Heterocyclic Chemistry, Vol. 54
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).
FROMAMINES A N D DIALKYL 1-ALKOXYALKYLIDENEMALONATES The reactions of amines and dialkyl alkoxymethylenemalonates are most frequently used to prepare the aminomethylenemalonates. Dialkyl alkoxymethylenemalonates react smoothly with amines under a wide variety of reaction conditions, usually with high yields (Scheme 6). The reactions probably proceed by an addition-elimination mechanism. In some cases, the addition products have been successfully isolated. 4-triazole was reacted with diethyl ethoxymethylenemalonate (EMME) in aqueous ethanol at ambient temperature for two days, an addition product (24) was obtained in 38% yield instead of a condensation product (62JCS2222).
4-Amino-2,2,6,6-tetramethylpiperidine was reacted with EMME in ethanol at ambient temperature to yield (4-piperidiny1amino)methylenemalonate (36)(77GEP2612314). Sec. A. I ] 25 SYNTHESES and diThe reaction of methyl 2-amino-2-deoxy-a-~-glucofuranoside methyl methoxymethylenemalonate in water for 5 h gave aminomethylenemalonate (37) in 92% yield (87MI4). + %OMe NHZ 500Me MeOCH=$ water COOMe On reaction with EMME in methanol at ambient temperature, glycosylamines gave N-glycosylaniinomethylenernalonates(38)in 8-44% yields was pre(68MI 1).
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)