Advances in Heterocyclic Chemistry, Vol. 52 by Alan R. Katritzky

By Alan R. Katritzky

This quantity, a part of a sequence on heterocyclic chemistry, is anxious with medicinal chemistry, the place derivatives of aminomethylenemalonates are key intermediaries within the synthesis of antimalarial brokers and likewise fulfil different features, reminiscent of being anticoccidials to be used in breathing infections, bone, joint and pores and skin infections and as antibacterial brokers. The publication additionally covers nineteenth century paintings at the constitution of aminomethylenemalonates, synthesis, different reactions and up to date study.

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308) may also be prepared by a Dimroth-type rearrangement of 1,2,4-triazolo[3,4-b]quinazolines(307) (86JHC833)upon heating with aqueous alkalies. (3g) (27) Finally, the reduced 1,2,4-triazolo[S,l-b]quinazolin-9-ones (310) were prepared from 1,2,4-triazole precursors when 3-amino-1,2,4-triazole(309) was cyclocondensed with 2-ethoxycarbonylcyclohexanones (72MI1; 890PP163). HZN + y2> HN-N _t. 0 0 (LO) 4.

G. 293)was prepared from 1,2,4-triazoleprecursors, such as 3-amino-l,2,4-triazole (292) by condensation with the 2-(Npheny1amino)methylene-1,3-~yclohexanedione(291) (70MI4). Pertinent 54 MOHAMMED A. E. SHABAN et 01. [See. B to this synthesis is the reaction of 3-amino-I ,2,4-triazoles (294)with 2hydroxymethylenecyclohexanone [79JCS(P1)3085]or ethyl 2-oxocyclohexanecarboxylate (890PP163) to yield a mixture of the angular 1,2,4triazolo{5,l-a]quinazolines (295) and the linear 1,2,4-triazol0[5,1-6]quinazolines (2%); yields of the latter predominated the former.

SHABAN et a / . [Sec. A H2NncN amcN -2H20 TSA ~ N' Formation of both heterocyclic rings of 104 was accomplished upon reaction of acetonylbenzoxainones(103) with hydrazine (62GEP1139123). g. 105), which involves the formation of both heterocyclic rings, is the cyclocondensation of anthraniloylhydrazines with P-ketoesters [60GEP1111505; 61GEPll20455; 80EUP15065; 81JMC735, 81USP4261996; 84M12; 88IJC(B)342], diethyl malonate [831JC(B)496], or diethyl acetylenedicarboxylate (79JHC957; 82FES719). The 4,9-dihydropyrazol0[5,1-b]quinazolines (107)were prepared by the reaction of phenyl isocyanate with the a-substituted phosphoranes 106 (84JOC1964; 87JOC1810).

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