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 serious significance in heterocyclic synthesis and feature been utilized in the instruction of a truly big range of heterocycles. The chemistry of this team of compounds has no longer 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 biggest sections, the applying of the aminomethylenemalonates to heterocyclic synthesis...
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Extra info for Advances in Heterocyclic Chemistry, Vol. 54
Equiv. (80MI2; 85EUP134165, 85FRP2548664; 86FRP2574404) and 2 mol. equiv. 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).
5-, 6-, 7-, and &Amino- 1,4-benzothiazines (83) were reacted with EMME at 100-120°C for 60-90 min to give I ,4-benzothiazinylaminomethylenemalonates (84) in 24-91% yields (84MI6). The reaction of l-amino-5-benzyl-5,8-dihydropyrido[4,3-~pyrimidin8-one and EMME in boiling DMF for 4 hr gave N-(pyridopyrimidin-Iy1)aminomethylenemalonate (85) in 48% yield (84KGS532). 36 [Sec. 1 ISTVAN HERMECZ et al. RkNQNH+ - R1kinFooEt EMME O H NH-CH=C O I79 1 H ( 80 1 tOOEt FOOEt (83) 6-NHz,R=H, Et 7-NH2. 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).
I N H $OOEt N0 NH-CH? (98) COOEt The reaction of 3-amino-] ,2,4-triazolo[3,4-b]benzoxazole and EMME in boiling ethanol for 2 hr gave condensation product 99 in 84% yield (89H925). 5 hr to give N-(pyrazolothienopyridin-3-y1)aminomethylenemalonate(101) in 50% yield. When the amine (100) and EMME were reacted in boiling acetic acid for 14 hr, instead of the expected cyclocondensation, only condensation occurred to give the aminomethylenemalonate (101) (83M 1079). FOOEt 0 ” (101 I (100) ( 102 (103) tOOEt Sec.