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 significant value in heterocyclic synthesis and feature been utilized in the guidance of a truly big variety of heterocycles. The chemistry of this staff of compounds has no longer been reviewed in additional than 50 years. the current therapy through Istvln Hermecz and co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. presents a entire 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 54
Depending on the molar ratio, the reactions of p-phenylenediamines and EMME gave N-(4-aminophenyl)aminomethylenemalonates (167) (86EUP174832) or 1 ,Cbis(aminomethylenemalonates) (168) (49JCS1017; 86EUP174832). EtOOC (168 I (167 1 2,3-Diamino-6-[(2,4,6-trimethylphenyl)methylamino]pyridine was reacted with EMME in boiling dioxane for 30 min to give 3-pyridylaminomethylenemalonate (169)in 73% yield (79CZ387). 4-Diaminopyridine was reacted with 2 mol. equiv. of EMME at 100°C for 5 hr to give 3,4-bis(aminomethylenemalonate) (170)in 30% yield (59JA6297).
A. 1 reflux for 8 hr or in boiling benzene in the presence of Triton B for 30 min (85BEP902586). (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).
Of EMME (54JA1109; 64JMC68; 72GEP2220294; 83JHC681; 86EUP174832), respectively. Depending on the molar ratio, the reactions of p-phenylenediamines and EMME gave N-(4-aminophenyl)aminomethylenemalonates (167) (86EUP174832) or 1 ,Cbis(aminomethylenemalonates) (168) (49JCS1017; 86EUP174832). EtOOC (168 I (167 1 2,3-Diamino-6-[(2,4,6-trimethylphenyl)methylamino]pyridine was reacted with EMME in boiling dioxane for 30 min to give 3-pyridylaminomethylenemalonate (169)in 73% yield (79CZ387). 4-Diaminopyridine was reacted with 2 mol.
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)