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 wide array of heterocycles. The chemistry of this team of compounds has no longer been reviewed in additional than 50 years. the current therapy by means of 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 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 appliance of the aminomethylenemalonates to heterocyclic synthesis...
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 54
Sample text
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. equiv. of EMME in boiling ethanol t o give bis(aminomethylenemalonate) (158) in 43% yield (64JMC68). Bis(pheny1amines) (159) were reacted with EMME to give bis(aminomethylenemalonates) (160) (64JMC68; 84MI1, 84MI5; 86MI 12). EtOOC COOEt 7-Amino- 1-(3-aminophenyI)-S-methyl[1,2,4]triazolo[4,3-a]quinoline was reacted with EMME by heating on a steam-bath for 3 hr to give the corresponding bis(aminomethylenema1onate) (161) (86EUP 174833).
0 hr I-cyclohexenylaminomethylenemalonates(43) were obtained in only moderate yields [82JAP(K)l16048]. 0 hr to afford (I-oxocycloheptatrien-2- and 5y1amino)methylenemalonates (44 and 45) in good yields (83USP438 1304, 83USP4382088). Sec. 11 27 SYNTHESES 5OOEt R+S:+ EMME - a;-CH=jOOE R = H,CI,Br, NMeAc (44I 5-Aminosalicylamide reacted readily with EMME in boiling benzene for 4 hr to give aminomethylenemalonate in 75% yield, but the reactions of 4aminosa1ic:ylamide and 4-arninosalicylic acid with EMME in boiling benzene or xylene for 4-24 hr were unsuccessful (75IJC1275).
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.