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. Author manuscript; available in PMC: 2011 Sep 29.
Published in final edited form as: J Am Chem Soc. 2010 Sep 29;132(38):13203–13205. doi: 10.1021/ja106901u

Table 3.

Formal [2 + 2 + 2] Cycloadditions via Propargylic Cyano Ene/Azadiene Diels-Alder Reactions

graphic file with name nihms-234331-t0006.jpg
entry Z R conditions product yield (%)a
1 17 MeN CH3 115 °C, 41 h 22 74
2 18 MeN H 160 °C, 36 h 23 58
3 19 O CH3 150 °C, 20 h 24 62
4 20 O H 210 °C, 6 h 25 35
5 21 CH2 CH3 170 °C, 14 h – 0b
a

Isolated yield of products purified by chromatography.

b

Ynone type [4 + 2] cycloadduct 27 was obtained in 91% yield (eq 2).