By Alan R. Katritzky (Ed.)
(from preface)Volume fifty four of Advances in HeterocycUc Chemistry is a monograph quantity, i.e., it truly 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 big range 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. presents a accomplished overview.After an introductory part, paintings from the nineteenth century is in brief thought of and next sections speak 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 resources for Advances in Heterocyclic Chemistry, Vol. 54
75-2 hr to give (1,4-benzothiazin-4-yl)rnethylenemalonates(141) [85JAP(K)208987;87JMC4651. Hexahydro-3-benzazocine was reacted with EMME in boiling ethanol for 1 hr to give the 3-benzazocinylmethylenemalonate(142) in 95% yield (74USP3840522). ISTVAN 50 HERMECZ et al. [Sec. 1 COOEt The reactions of hexahydrocarbazoles (143, R2 = H) and EMME at 110°C for 30 min afforded 9-carbazolylmethylenemalonates(144, R2 = H) in good yields (79GEP2849158,79GEP2914218,79GEP2914258). The reaction of 4a-hydroxy-1,2,3,4,4a,9a-hexahydrocarbazole(143, R = R' = H,R2 = OH) and EMME gave 9-carbazolylmethylenemalonate (144, R = R' = H,R2 = OH), which was dehydrated to the corresponding diethyl (1,2,3,4-tetrahydrocarbazol-9-yl)methylenemalonatein methanol in the presence of picric acid (60JA4404).
L The reaction of propylamine derivatives (30) with EMME gave aminomethylenemalonates (31) in 80-84% yields (82MI7). Aminomethylenemalonates (32) were prepared in the exothermic reaction of glycine esters and EMME (77H1821). The sodium salt of D-phenylglycine was reacted with EMME in boiling benzene for 3 hr, and the ethanol was then azeotropically removed to give the sodium salt of the aminomethylenemalonate (33) in 50% yield [80JAP(K)3 1040; 8 1 CPB 1998; 86MI21. The mono- and disodium salts of Cephalosporin C were reacted with EMME in aqueous acetone at room temperature for 5-6 hr to give aminomethylenemalonate (34) (80GEP3002659; 82EUP45717).
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).
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)