Synthesis of new spiro compounds proceeding from 11H-Indeno[1,2-b]quinoxalin-2-one

Abstract

Reaction of 11Н-indeno[1,2-b]quinoxalin-2-one with semi(thiosemi)carbazides in ethanol resulted in semi(thiosemi)carbazones which at boiling in acetic anhydride underwent cylization yielding N-{3'-acetyl-3'Н-spiro[indeno[1,2-b]quinoxalin-11,2'-[1,3,4]oxa(thia)diazol]-5'-yl}acetamides. Aldol crotonic condensation of 11Н-indeno[1,2-b]quinoxalin-2-one with methyl N-(4-acetylphenyl)carbamate afforded the corresponding chalcone that at boiling in anhydrous ethanol with hydrazine hydrate for 1 h formed a spiro compound with a pyrazole ring. Five-component condensation of ninhydrin, 1,2-phenylenediamine, sarcosine, malononitrile (or ethyl cyanoacetate), and 4-formylphenyl N-phenylcarbamate in a mixture EtOH -[bmim]Br led to the formation ofwidely used for preparation of diverse derivatives exhibiting a wide range of biological activity. Its oxime is a noncytotoxic inhibitor of inflammatory cytokine and of production of nitrogen monoxide [1]. Schiff bases obtained from the 11Н-indeno[1,2-b]quinoxalin-2-one are highly cytotoxic and possess antiviral activity [2]. Spiro compounds with the 11Н-indeno[1,2-b]quinoxaline fragment are of practical interest. Chalcones preparation by aldol crotonic condensation of 11Н-indeno-[1,2-b]quinoxalin-2-one with acetophenones was described and their transformation into spiro compounds with cyclopropane and pyrazole rings was investigated [3, 4]. The synthetic methods for derivatives of indeno[1,2-b]quinoxaline spiro-jointed with other heterocyclic fragments are insufficiently developed.Boiling of equimolar quantities of semi(thiosemi)carbazides with compound 1 in ethanol afforded semi-(thiosemi)carbazones of 11Н-indeno[1,2-b]quinoxalin-2-one 2 and 3 in 95-97% yields. The structure and the composition of compounds 2 and 3 was proved by IR spectra and elemental analyses (Scheme 1).Semi(thiosemi)carbazones of cyclic ketones are known to by capable of heterocyclization with the formation of spiro compounds [5]. We explored the possibility to prepare new spiro compounds from semi-

Recent advancement in the synthesis of diverse spiro-indeno[1,2-b]quinoxalines: a review

“…Later on, this reaction was studied by Velikorodov et al 59 The regioselectivity of the process is very interesting and depends upon the nature of substituents present on the aromatic ring of dipolarophile molecule 41. The threecomponent reaction of dinitriles 41 with an unsubstituted benzene ring or electron-withdrawing substituents (Cl, NO 2 ), Lproline 16d and quinoxalinones 3 (X ¼ CH, N) produced spiropyrrolizidines 42 (56-86% yields) with unexpected regioselectivity.…”

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

“…[271] An easily obtainable from indenoquinoxalin-2-one 281 semi-or (thiosemi)carbazones 290 at boiling in acetic anhydride underwent cyclization yielding spiro indenoquinoxalines 291 (Scheme 76). [282]…”

Modified 7-Chloro-11H-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities

“…Meanwhile, Yang et al [2] discussed the efficient regioselective synthesis of novel functionalized dispiropyrrolidines via a three-component (3 + 2) cycloaddition reaction with a yield of approximately 87%. Additionally, other studies have shown a desired synthetic route for Spiro indeno [1,2-b]quinoxaline-11,3 -pyrrolizidine derivatives [8]. These various approaches were considered for the higher yield of the final compounds including multicomponent derivatives of the heterocyclic Spiro compounds.…”