75608-94-5Relevant academic research and scientific papers
Selective intermolecular photo-[4 + 4]-cycloaddition with 2-pyridone mixtures. 2. Preparation of (1α,2β,5β,6α)-3-butyl-9-methoxy-3,7- diazatricyclo[4.2.2.22,5]dodeca-9,11-diene-4,8-dione
Sieburth, Scott McN.,Lin, Chao-Hsiung,Rucando, David
, p. 950 - 953 (1999)
Photochemistry of 2-pyridone mixtures can be selective and thereby lead to useful quantities of [4 + 4] cycloaddition cross products. The selective intermolecular reaction described here employs an excess of 4-methoxy-2- pyridone (6), which does not photodimerize but will undergo [4 + 4] cycloaddition with 2-pyridones without a 4-methoxy group such as N-butyl-2- pyridone 12. Isolated yields of the trans product (1α,2α,5β,6α)-3-butyl- 9-methoxy-3,7-diazatricyclo[4.2.2.22,5]dodeca-9,11-diene-4,8-dione (7) are very sensitive to the ratio of the two starting pyridones, and this product has been isolated in yields of up to 51%. This photoreaction produces, in a single step from simple aromatic precursors, a tricyclic product with four stereogenic centers and four distinct functional groups.
