Annulation Reactions Catalyzed by Amberlite-Bound Hexafluorophosphate

Yasuhiro Uozumi; Makoto Nagaosa

doi:10.1055/s-0032-1317917

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Synfacts 2013; 9(1): 0113
DOI: 10.1055/s-0032-1317917

Polymer-Supported Synthesis

Annulation Reactions Catalyzed by Amberlite-Bound Hexafluorophosphate

Rezensent(en):

Yasuhiro Uozumi

,

Makoto Nagaosa

Ghosh P, * Mandal A. University of North Bengal, Darjeeling, India
Synthesis of Functionalized Benzimidazoles and Quinoxalines Catalyzed by Sodium Hexafluorophosphate Bound Amberlite Resin in Aqueous Medium.

Tetrahedron Lett. 2012;
53: 6483-6488

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Publikationsverlauf

Publikationsdatum:
17. Dezember 2012 (online)

Abstract
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Key words

catalysis - Amberlite - diamines - benzimidazoles - quinoxalines

Significance

Amberlite resin-bound hexafluorophosphate (Amberlite-PF₆) was prepared by treatment of Amberlite 900 with aqueous NaPF₆ (eq. 1). In the presence of Amberlite-PF₆, the annulation of phenylenediamines 1 with aldehydes 2 took place to give the corresponding benzimidazoles 3 (25 examples, 72–96% yield).

Comment

The binding of hexafluorophosphate on Amberlite resin was confirmed by IR spectra (557 and 832 cm^–1), though other characterizations were not given. Phenylenediamines 1 also reacted with α-bromoketones 4 in the presence of Amberlite-PF₆ to give the corresponding quinoxalines 5 via an aromatization step.

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