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In a study directed toward the sysnthesis of benzothiazoles via cyclization of o-bromophenylthioureas, two benzimidazolones were prepared by Pd-catalyzed urea cyclization under relatively harsh conditions/high catalyst loadings; see: Benedi, C.; Bravo, F.; Uriz, P.; Fernández, E.; Claver, C.; Castillón, S. Tetrahedron Lett. 2003, 44, 6073-6077.
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20
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33746916659
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note
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Notably, the published procedures advocate a "normal" addition protocol, in which CSI is added to the substrate. Based on the observations from the current work, this could account for the moderate yields obtained in these cases.
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21
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33746883768
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note
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Attempted thermal cyclizations in a variety of solvents (DMSO, MeCN, NMP, water, toluene, i-PrOH, DMAc, pyridine, n-BuOH, and AcOH) were not successful, generally returning unchanged starting material.
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22
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0034794463
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Cu-catalyzed conditions were less successful for this reaction, affording only 67% conversion of starting material. See: Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
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Klapars, A.1
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23
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33746902625
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note
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Again, the mass balance was found in the urea cleavage side reaction, apparently suppressed under the less basic conditions.
-
-
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24
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33746907307
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note
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2 was also ineffective in attempts to cyclize the bromoaniline substrate.
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