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 serious value in heterocyclic synthesis and feature been utilized in the instruction of a really good selection of heterocycles. The chemistry of this staff of compounds has no longer been reviewed in additional than 50 years. the current remedy via 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 applying of the aminomethylenemalonates to heterocyclic synthesis...
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 54
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).
Syntheses of Dialkyl 1-Aminoalkylidenemalonates 1. FROMAMINES A N D DIALKYL 1-ALKOXYALKYLIDENEMALONATES The reactions of amines and dialkyl alkoxymethylenemalonates are most frequently used to prepare the aminomethylenemalonates. Dialkyl alkoxymethylenemalonates react smoothly with amines under a wide variety of reaction conditions, usually with high yields (Scheme 6). The reactions probably proceed by an addition-elimination mechanism. In some cases, the addition products have been successfully isolated.
5-24 hr to give N-(tetrahydroisoquinolin-3yl)aminomethylenemalonates in 82-87% yields (83KGS1279; 84KFZ93 1). 3-Benzothiopyranylaminomethylenemalonates(73) were prepared in 7848% yields in the reactions of 3-aminothiochromones and EMME at 140°C for 5 hr under nitrogen (85JHC89). (711 R (721 R=H,CN W NH2 + EMME - R R = H , 6-Me ,8-Me 500Et W NH-CH=$ 0 tOOEt (73) 2-Amino-] ,4- and 4-amino-] ,2-naphthoquinones (74 and 75) failed to react with EMME, probably because of the “amide-like” character of the amino group.
Advances in Heterocyclic Chemistry, Vol. 54 by Alan R. Katritzky (Ed.)