Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)

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 significance in heterocyclic synthesis and feature been utilized in the practise of a really big 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 co-workers, Geza Kareszturi and Lelle Vasv^ri-Debreczy. offers a entire 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 biggest sections, the appliance of the aminomethylenemalonates to heterocyclic synthesis...

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Sec. 11 27 SYNTHESES 5OOEt R+S:+ EMME - a;-CH=jOOE R = H,CI,Br, NMeAc (44I 5-Aminosalicylamide reacted readily with EMME in boiling benzene for 4 hr to give aminomethylenemalonate in 75% yield, but the reactions of 4aminosa1ic:ylamide and 4-arninosalicylic acid with EMME in boiling benzene or xylene for 4-24 hr were unsuccessful (75IJC1275). However, if the sodium salt of 4-aminosalicylic acid was reacted under similar conditions, the required aminomethylenemalonate (46)was obtained. 4-Fluoro-3-(2-methyl-I ,3-dithian-2-yl)aniline was reacted successfully with EMME in toluene.

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). 5-5 hr [81FRP2463771, 81FRP2476079; 81JAP(K)55388, 8 1 JAP(K)59773; 82BEP89 1046, 82BEP891537; 83EUP79 162, 83JAP(K)2- 47 SYNTHESES Sec.

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).

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