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 significant value in heterocyclic synthesis and feature been utilized in the coaching of a really large choice of heterocycles. The chemistry of this crew of compounds has no longer been reviewed in additional than 50 years. the current therapy by way of Istvln Hermecz and co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. presents a complete 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 houses of the aminomethylenemalonates, theirprepa-ration, and, within the biggest sections, the applying of the aminomethylenemalonates to heterocyclic synthesis...
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Extra info for Advances in Heterocyclic Chemistry, Vol. 54
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).
A. I N H $OOEt N0 NH-CH? (98) COOEt The reaction of 3-amino-] ,2,4-triazolo[3,4-b]benzoxazole and EMME in boiling ethanol for 2 hr gave condensation product 99 in 84% yield (89H925). 5 hr to give N-(pyrazolothienopyridin-3-y1)aminomethylenemalonate(101) in 50% yield. When the amine (100) and EMME were reacted in boiling acetic acid for 14 hr, instead of the expected cyclocondensation, only condensation occurred to give the aminomethylenemalonate (101) (83M 1079). FOOEt 0 ” (101 I (100) ( 102 (103) tOOEt Sec.
Substituted pheny1amino)methylenemalonates (48) were prepared in the reaction of 2-(5-amino-2alkoxyphenyl)-8-azapurin-6-onesand EMME at 140°C (78GEP2747199; 82SZP627755). Ethyl 2-aminopyridinecarboxylates reacted smoothly with EMME at 120-130°C in 30 min, except the 3-carboxylate, which was reacted at 150- 170°C to give the corresponding 2-pyridylaminomethylenemalonate (49) in 78-92% yields (78MI5). 2-Amino-3-(N,N-dimethylcarbamoyl)thiopyridinewas reacted with EMME or di-(Cmethoxybenzyl) (4-methoxybenzyloxy)methylenemalonate at 100- 120°C for 1 hr to afford 2-pyridylaminomethylenemalonates (50) in 76 and 80% yields, respectively (86EUP218423).