Solution phase sythesis of arylbenzoxazoles

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S217000

Reexamination Certificate

active

06861533

ABSTRACT:
This invention provides methods for the solution-phase synthesis of arylbenzoxazoles. The methods involve condensation of aminophenols with benzaldehydes to form a Schiff base. The Schiff base is then induced to undergo oxidative cyclization in the presence of DDQ. The resulting arylbenzoxazoles can be separated from the reduced DDQ byproduct by treatment of reaction mixture with a strongly basic ion exchange resin.

REFERENCES:
patent: 0806419 (1997-11-01), None
patent: WO 9846594 (1998-10-01), None
Varma, R. S.; Saini, R. K.; Prakash, O. “Hypervalent Iodine Oxidation of Phenolic Schiff's Bases: Synthesis of 2-Arylbenzoxazoles” Tetrahedron Letters, 1997, 38(15), 2621-2622.*
Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. New York: John Wiley & Sons, Inc. 2001, p. 1511.*
Li, P.; Gi, H.-J.; Sun, L.; Zhao, K. “Oxidative Conversion of Isoxazolidines to Isoxazolines” J. Org. Chem. 1998, 63, 366-369.*
Sate et al.,The Journal of Antibiotics, 54:1: 102-104 (2001).
Temiz et al.,II Farmaco, 53: 337-341 (1998).
DeLuca et al.,Tetrahedron Letters, 38:2: 199-202 (1997).
Wang et al.,Tetrahedron Letters, 38:37: 6529-6532 (1997).

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