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 significant value in heterocyclic synthesis and feature been utilized in the training of a really big choice of heterocycles. The chemistry of this workforce of compounds has now not been reviewed in additional than 50 years. the current therapy 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 short thought of and next sections speak about in flip the constitution and physicochemical homes of the aminomethylenemalonates, theirprepa-ration, and, within the greatest sections, the appliance of the aminomethylenemalonates to heterocyclic synthesis...

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H (155 1 EMME oa1,. I CHK-COOEt I 1156) COOEt 52 ISTVAN HERMECZ et al. [Sec. A . l c . From Polyamines Depending on the reaction conditions and molar ratio, mono- and bis(aminomethy1enemalonates)can be obtained in the reactions of dialkyl alkoxymethylenemalonates and bisamines. The reaction of I ,2-diaminoethane and EMME was carried out in boiling ethanol or in a mixture of diethyl ether and ethanol at -5°C to give bis(aminomethy1enemalonate) (157) in 72% and 64% yields (64JMC68; 67M11). HfiCH2CHzNH2 + Z EMME EtOO{ {OOEt C=CH-NHCH,CH,NH-CH=$ EtOOt COOEt 1157 I A EtoH PhCH2NHCHzCHzNHCHzPh + ZEMME PhC Hz- N-CH=C- COOEt (Hz tOOEt A EtOH FH2 COOEt PhCHz-t&CH=t-COOEt 1 158 ) 1,2-Bis(benzylamino)ethylene was reacted with 2 mol.

2-(Cyclopropylamino)-6(4-ethoxycarbonylpiperazino)-5-fluoropyridinewas reacted in boiling xylene for 24 hr to afford the corresponding 2-pyridylaminomethylenemalonate (111)in 39% yield (85EUP153163,85EUP153828,85EUP159174; 86EUP172651; 88EUP265230). 3-Methylamino-6-morpholinopyridazinewas reacted with EMME at 120°C for 2-3 hr to afford diethyl N-methyl-N-(6-morpholino-3pyridazi-ny1)-aminomethylenemalonate in 54% yield (88JHC 1535). N-Ethyl-3,4-methylenedioxyanilinewas reacted with EMME in boiling dioxane for 6 hr, in the presence of two drops of a solution of 40% Triton B in methanol, to give N-ethyl-N-(3,4-methylenedioxyphenyl)aminomethylenemalonate in 87% yield [71JAP34707; 72JCS(P1)173].

Ciprofloxacin was reacted with EMME in aqueous dioxane in the presence of sodium hydroxide at ambient temperature for 5 hr to give aminomethylenemalonate (120) in 48% yield (84GEP3306772, 84GEP3308908). 5 hr to afford 1-indolinylmethylenernalonates (122) [83JAP(K)I3585, 83JAP(K)9051I]. Indolines (123) were condensed with EMME at R eF* R + EMME - R=CI,F (121 1 n NCHZCF, W -N -( 3 0 1 - 1 F&Me CHX-COOEt tOOEt ISTVAN HERMECZ et al. 46 [Sec. A . l 1 10-120°C to give I-indolinylmethylenemalonates(124)(79GEP2914218, 79GEP2914258).

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