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 serious significance in heterocyclic synthesis and feature been utilized in the guidance of a truly big range of heterocycles. The chemistry of this staff of compounds has now not been reviewed in additional than 50 years. the current therapy through Istvln Hermecz and co-workers, 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 talk about in flip the constitution and physicochemical houses of the aminomethylenemalonates, theirprepa-ration, and, within the greatest sections, the applying of the aminomethylenemalonates to heterocyclic synthesis...
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 54
Sec. A. I SCHEME 21 The reaction of N-(2,2,2-trifluoroethyl)-3,4-methylenedioxyaniline and EMME at 140-150°C for 3 hr gave diethyl N-(2,2,2-trifluoroethyl)-N-(3,4methy1enedioxyphenyl)aminomethylenemalonate (76GEP2534869). 0 hr (69BRP1147336). 2-Anilinoquinolines (113) were reacted with EMME to give N-(2quinoliny1)-N-phenylaminomethylenemalonates (114)(87JIC48I ). In the reaction of EMME and the potassium salt of pyrrole in tetrahydrofuran (THF) at 0°C for 30 min, an addition product, ethoxy(1-pyrroly1)methylmalonate (115),could be isolated in 85% yield (82CB714).
STVAN 26 R:OH. R1=Rz:H, HERMECZ et al. [Sec. l i RLMe,Et w O"[ R= d = O M e , OEt. R1:Rz=H 0c OR 3 dR R =R2=H, R'=OMe, R3=Me (40) I-Amino-I-deoxy-D-fructose acetate was reacted with dimethyl methoxymethylenemalonate in the presence of sodium carbonate in water at ambient temperature for 4 hr to give aminomethylenemalonate (19) in 97% yield: several isomeric forms were present both in the solid state and in solution (86MI10) (see Table IV and Scheme 5B). The reaction of D-ribosylamine and EMME in methanol at room temperature for 48 hr afforded a mixture of N-(@-D-ribopyranosy1)-and N-(@-Dribofuranosy1)aminomethylenemalonates (41 and 42) in 48 and 8% yields, respectively (88MII).
0 hr to give condensation products (140) in good yields [82JAP(K)2030851. 75-2 hr to give (1,4-benzothiazin-4-yl)rnethylenemalonates(141) [85JAP(K)208987;87JMC4651. Hexahydro-3-benzazocine was reacted with EMME in boiling ethanol for 1 hr to give the 3-benzazocinylmethylenemalonate(142) in 95% yield (74USP3840522). ISTVAN 50 HERMECZ et al. [Sec. 1 COOEt The reactions of hexahydrocarbazoles (143, R2 = H) and EMME at 110°C for 30 min afforded 9-carbazolylmethylenemalonates(144, R2 = H) in good yields (79GEP2849158,79GEP2914218,79GEP2914258).
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)