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 significance in heterocyclic synthesis and feature been utilized in the education of a truly large choice of heterocycles. The chemistry of this staff of compounds has now not been reviewed in additional than 50 years. the current remedy by way of Istvln Hermecz and associates, 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 greatest sections, the appliance of the aminomethylenemalonates to heterocyclic synthesis...
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Additional info for Advances in Heterocyclic Chemistry, Vol. 54
R = H , E t 8-NH2, R = H , Et (84) N-(4H-1,2,4-Benzothiadiazine 1 , l -dioxide-3-yl)aminomethylenemalonates (86) were prepared in 90-92% yields in the reactions of 3-aminodH1,2,4-benzothiadiazine 1,l-dioxides and EMME at 170-180°C for 2 hr (89JHC473). 6-Aminobenzo[b] thiophenes (87) were reacted with EMME at 1 10- 140°C to give N-[benzo [b]thien-6-yl]aminomethylenemalonates in 91-93% yields (88AP241). Sec. A. I ] 37 SYNTHESES 4- and 5-Amino-2-phenyl-1,3,-dioxoisoindoles were reacted with EMME to afford N-(2-phenyl-l,3-dioxoisoindolyl)aminomethylenemalonates (88) (87MI I).
Sec. A. 1 5-Amino-2,3-dimethyl-3H-imidazo[4,5-b]pyridine was reacted with EMME in boiling toluene for 2 hr to afford N-(imidazopyridin-5-yl)aminomethylenemalonate (91)in 84% yield (86EUP174832). The reaction of 3aminod,6-dimethyl- lH-pyrazolo[3,4-b]pyridineand EMME yielded N(4,6-dimethyl- 1H-pyrazolo[3,4-b]pyridin- 3- yl)aminomethylenemalonate (92) (87MI5). N' + EMME - COOEt 1921 In the reaction of adenine and EMME in the presence of triethylamine in boiling dimethylformamide for 16 hr, 6-purinylaminomethylenemalonate was obtained in 75% yield (86EUP174832) (Scheme 17).
H O ~ C ~ N H - C COOEt H=( COOEt HO HO H The reaction of I-amino-I-cyclohexen-3-oneswith EMME in the presence of p-toluenesulfonic acid at 120-135°C for 2-18 hr gave Ncyclohexenylaminomethylenemalonates ( 4 3 in 71-93% yields [75JHC 1245; 79JAP(K)I 19484; 80GEP2947948, 80GEP3008884; 82JHC2891. 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).
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)