Readily accessible 2‐aryloxybenzaldehydes and 2‐(arylthio)benzaldehydes undergo a sequence of reactions leading to a wide variety of unsubstituted 9H‐xanthenes and thioxanthenes in high yields when heated with a Lewis acid in diisopropyl ether. This reductive cyclization method is compatible with several important functional groups. The method is also applicable for the selective reductive cyclization of the more electron‐rich aryl ring of a 2,6‐bis(aryloxy)benzaldehyde. The key feature of this transformation is the chemoselective reduction of a transient xanthylium ion in the presence of aldehydic group via intermolecular hydride transfer from diisopropyl ether (solvent).
An efficient and environmentally benign domino protocol has been presented for the synthesis of structurally diverse spiroheterocycles spiroannulated with 1,3,4‐thiadiazolo[3, 2‐a]pyrimidine involving three‐ component reaction of 2‐amino‐1,3,4‐thiadiazole, isatin/N‐methyl‐4‐piperidone/1,2‐acenaphthylenedione and carbonyl compounds catalyzed by magnetically recoverable and reusable nanocrytalline sulfated zirconia (Fe3O4@ZrO2/SO42−) under solvent free conditions with grinding at room temperature. The use of magnetically recyclable and reusable catalyst, mild reaction conditions with operational simplicity (grinding), and excellent product yields are significant features of the present synthetic protocol. Moreover, easy magnetic separation of the catalyst eliminates the requirement of catalyst filtration after completion of the reaction and the catalyst remains highly active even after recycled several times.
A concise and practical approach for expedient synthesis of substituted benzoxazolpyrrole, benzothiazolpyrrole and indolizine by three-component cascade annulative coupling of aldehyde, 2-hetaryl acetonitrile and isocyanide in the presence of 10...
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