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 coaching of a really 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 means 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 short thought of and next sections speak 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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Additional resources for Advances in Heterocyclic Chemistry, Vol. 54
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).
Al. (89CCC713), but for characterization of the product, they gave different melting points (102-104°C vs. 89-91°C). 38 ISTVhN HERMECZ et d. [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).
H (125 1 n:O,l; R:H,Me; R’=H,Me; COOR’ 1126) R h E t , ii3u , hexyl R = H , C l ; R’= H . C l , (127 too~t R2= H , C l , OSOfle , OSO2C,H,-4Me ((Tetrahydroquinolin-1-y1)methylenemalonates (127) were prepared in the reactions of tetrahydroquinolines and EMME at 1 10-120°C [79GEP29142 18, 79GEP29 14258; 80JAP(K)38364]. Tetrahydroquinolines (l28)were reacted with EMME at 120-180°C for 1-3 hr to give (tetrahydroquinolin- 1-y1)methylenemalonates(129) (73GEP2264 163; 74GEP2415763; 76MIP3, 76USP3969463, 76USP397665 1, 76USP3985753, 76USP3985882; 77USP400 1243, 77USP40 14877).
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)