By Alan R. Katritzky (Ed.)

ISBN-10: 0120207540

ISBN-13: 9780120207541

(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 significance in heterocyclic synthesis and feature been utilized in the instruction of a truly big variety of heterocycles. The chemistry of this team of compounds has now not been reviewed in additional than 50 years. the current remedy via Istvln Hermecz and co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. offers a accomplished 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 applying of the aminomethylenemalonates to heterocyclic synthesis...

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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). The reaction of o-phenylenediamine (R = H) and 1 mol. equiv. of EMME at 100°C for 2 hr afforded diethyl N-(2-aminophenyl)aminomethylenemalonate (162, R = H) in 94% yield (57MI2; 59MI1). When 2 mol. equiv. of Sec. 11 53 SYNTHESES -q 9-y HZN HZN A + 2 EMME EtOOF EtOOC-C=HC-HN + EtOOC -6:HC-HN Me EtOOC q = y qN (161) Me EMME was applied and the reaction mixture was heated on a steam-bath for 4 hr, 1,2-bis(aminomethylenemalonate)(163, R = H) was obtained in 79% yield (46JA1320).

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.

Chapter 7 (Section C) lists the amines that have been reacted with alkoxymethylenemalonates (R3 = H). Aminomethylenemalonate (13)was prepared in 80% yield from diethyl (ethylthiomethy1ene)malonate with aqueous ammonium hydroxide at 0°C (52LA48). x% Me N NHNY +EMME All h SCHEME 10 23 SYNTHESES Sec. A . I ] SCHEME 11 a. From Primary Amines Tryptamine derivatives (26) were reacted with EMME to give N-[2-(3indolyl)ethyl]aminomethylenemalonates(27) in nearly quantitative yields (77H 1699; 79MI 1 ). + I?

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Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)


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