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. Author manuscript; available in PMC: 2009 May 7.
Published in final edited form as: Org Lett. 2007 Mar 16;9(8):1473–1476. doi: 10.1021/ol070163t

Table 1.

Conditions for pyridine formation from dienal 3b

graphic file with name nihms-63838-t0009.jpg
entry R conditions time temp (°C) yield (6b)
1 H NaOAc 24 h 90 80%
2 H NaOAc sealed tube 4 h 150 82%
3 H NaOAc microwave 1 h 150 98%
4 Me NaOAc, microwave 1 h 150 68%
5(a) H pyridine then AcCl 0.5 h 0-25 --(b)
(a)

Pyridine used as solvent

(b)

Acetoxy derivative of 4b isolated as only product in 69% yield.