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 coaching of a truly big variety of heterocycles. The chemistry of this team of compounds has no longer been reviewed in additional than 50 years. the current remedy through Istvln Hermecz and co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. presents a finished 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 homes of the aminomethylenemalonates, theirprepa-ration, and, within the greatest sections, the applying of the aminomethylenemalonates to heterocyclic synthesis...
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Additional info for Advances in Heterocyclic Chemistry, Vol. 54
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). 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).
Triethylamine in methanol (68MIl)l. , 46JA1232, 46JA1268, 46JA1317; 5OJCS464, 50JOC1224; 58JCS828; 70CPB1385). The most frequently applied dialkyl alkoxymethylenemalonate is EMME. , 75JAP(K)49286; Sec. , 74MIPI ; 76ACH91). , 52LA48) are also sometimes used (Scheme 7). , 76JCS(P1)1331]. , 75IJC 1275)(Scheme 8). , 64JMC68, 64JMC487; 70CPB1385; 77GEP2612314; 78GEP2737542). Both 2-nitroaniline and N-methylaniline react less readily than aniline with EMME, but if these two groups are present at the same time (N-methyl-2-nitroaniline was used), no reaction occurred at all (59JCS2401) (Scheme 9).
From Secondary Amines N-(Diphenoxyphosphinylmethy1)-N-(ethoxycarbonyl- and cyanomethy1)amines were reacted with EMME in boiling toluene under nitrogen for 16 hr to give aminomethylenemalonates (104) in 56 and 73% yields, respectively (84USP4444581, 84USP4444582). In the reactions of N-alkylN-arylamines (105) and EMME at 120-140°C for 20 min, N-alkyl-Narylaminomethylenemalonates (106) were prepared in 54-8 I% yields (72HCA I3 19). @yH FOOEt + COOEt N / Et SCHEME 19 R3 SOOEt @LYH+ EMME -QN-CH3 R’ 1105) R R’ (106) A COOEt R’=R2=R3= H R = M e , E t .