A Simple Synthesis of 2′,5′-Disubstituted-Spiro [Dihydroacridine 9(10H), 4′-Thiazolines] by the Reaction of Corresponding 3-(Acridin-9-Yl)-Thioureas with Methyl Bromoacetate and Bromoacetonitrile

Abstract

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Regioselective Synthesis of 2-Imino-1,3-thiazolidin-4-ones by Treatment ofN-(Anthracen-9-yl)-N′-ethylthiourea with Bromoacetic Acid Derivatives

“…16 MHz for 1 H, 125.78 MHz for 13 C and 50.69 MHz for 15 N. The spectra were recorded at 35°C and both 1 H and 13 C spectra were referenced internally to tetramethylsilane (δ ϭ 0 for both), whilst 15 N spectra were referenced externally to 90% nitromethane in CD 3 NO 2 (δ ϭ 0). 15 N chemical shifts reported to two decimal places were observed directly, whilst shifts reported at lower precision were observed indirectly.…”

Unexpected Formation of a Spiro Acridine and Fused Ring System from the Reaction between an N-Acridinylmethyl-Substituted Thiourea and Bromoacetonitrile under Basic Conditions

“…Structures incorporating the acridine moiety have shown marked mutagenic, antiviral, and antitumor − activities and are thus of prime interest for pharmaceutical applications. In our previous studies − a convenient synthesis of spiro acridine compounds was described. It also highlighted the particular susceptibility of the acridine C9 to nucleophilic attack and the subsequent ready formation of a five-membered ring.…”