Furopyridines.  XVIII  . Photocycloaddition of furo[2,3‐ c ]pyridin‐7(6 H )‐one with acrylonitrile | Zendy

Shiotani Shunsaku | Zendy; Tsukamoto Youichi | Zendy; Kawahara Yukiko | Zendy; Saitoh Hideo | Zendy; Ishida Toshimasa | Zendy; In Yasuko | Zendy

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Furopyridines. XVIII . Photocycloaddition of furo[2,3‐ c ]pyridin‐7(6 H )‐one with acrylonitrile

Author(s) -

Shiotani Shunsaku,

Tsukamoto Youichi,

Kawahara Yukiko,

Saitoh Hideo,

Ishida Toshimasa,

In Yasuko

Publication year - 1996

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570330666

Subject(s) - chemistry , acrylonitrile , adduct , pyridine , derivative (finance) , medicinal chemistry , crystal structure , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , economics , financial economics , copolymer , polymer

The photocycloaddition of furo[2,3‐ c ]pyridin‐7(6 H )‐one ( 1 ) and its N ‐mefhyl derivative ( 1‐Me ) to acrylonitrile has been studied. The structures of the photoadducts isolated by colum chromatography were determined by the nuclear magnetic resonance spectroscopy and single crystal X‐ray analysis. The cyclo‐addition of 1 afforded an adduct 2 at the carbonyl oxygen and 8‐cyano‐8,9‐dihydrofuro[ d ]azocin‐7(6 H )‐one ( 3 ), and the addition of 1‐Me the N ‐methyl derivative 3‐Me of 3 , (9 S *)‐9‐cyano‐6‐methyl‐3a,7a‐dihydro‐3a,7a‐ethanofuro[2,3‐c]pyridin‐7(6 H )‐one ( 4 ), (2 S *, 2a R *, 7b R *)‐ ( 5 ) and (1 R *, 2a S *, 7b S *)‐2‐cyano‐3‐methyl‐4‐oxo‐1,2,2a,3,4,7b‐hexahydrocyclobuta[ e ]furo[2,3‐ c ]pyridine ( 6 ).

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