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. Author manuscript; available in PMC: 2011 Oct 15.
Published in final edited form as: Org Lett. 2010 Oct 15;12(20):4686–4689. doi: 10.1021/ol102078v

Table 1.

DDQ-catalyzed oxidative cyclization reactions.a

entry substrate product time (h) yield (%)b
1 graphic file with name nihms-239805-t0005.jpg graphic file with name nihms-239805-t0006.jpg 41 76
2 graphic file with name nihms-239805-t0007.jpg graphic file with name nihms-239805-t0008.jpg 44 83
3 graphic file with name nihms-239805-t0009.jpg graphic file with name nihms-239805-t0010.jpg 40 92
4c graphic file with name nihms-239805-t0011.jpg graphic file with name nihms-239805-t0012.jpg 48 75
5 graphic file with name nihms-239805-t0013.jpg graphic file with name nihms-239805-t0014.jpg 36 68
6 graphic file with name nihms-239805-t0015.jpg graphic file with name nihms-239805-t0016.jpg 24 87
7 graphic file with name nihms-239805-t0017.jpg graphic file with name nihms-239805-t0018.jpg 40 70
8 graphic file with name nihms-239805-t0019.jpg graphic file with name nihms-239805-t0020.jpg 30 81
9 graphic file with name nihms-239805-t0021.jpg
a

Representative procedure: DDQ was added in three equal portions over the course of the reaction (0.15 equiv total) to a suspension of the substrate, 2,6-dichloropyridine (2 equiv), and activated MnO2 (6 equiv) in CH3NO2 (0.1 M). The reaction stirred at room temperature for the indicated period of time.

b

Yields refer to isolated, purified products.

c

Reaction required 0.2 equiv DDQ.