An unusual synthesis of N-unsubstituted benzazepinones

Organic Letters

Volumn 14, Issue 21, 2012, Pages 5514-5517

  Quiclet Sire, Béatrice ^a   Tran, Ngoc Diem My ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84868367264     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3026044     Document Type: Article

References (27)

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27. S.Z.Z. would like to put on record his debt to Prof. Ireland for being indirectly responsible for the discovery of a mild source of hydroxyl radicals: In the spring of 1989, I happened to be a visiting scholar at Texas A&M University when Bob Ireland was invited to give a seminar. During our brief meeting, he said he was interested in using the Barton decarboxylation reaction in one of his syntheses and asked if I could provide him with a reliable procedure for obtaining N -hydroxypyridine-2-thione from the commercial aqueous solution of its sodium salt. In those pre-internet days, I had to wait until I returned to France a couple of weeks later to retrieve the procedure from the thesis where it was detailed. I dutifully copied the procedure and decided to enclose a couple of grams of N -hydroxypyridine-2-thione, so that Bob Ireland's student would not have to wait to test the decarboxylation on his substrate. However, as I was about to place the sample in a small glassine envelope, Prof. Marcel Fétizon came by and we chatted at the door of my office. It was a grim and overcast day but, as we were chatting, the sun just came out for a few minutes and the sunlight struck the vial containing the N -hydroxypyridine-2- thione. When I eventually returned to my desk, I was dismayed to see that the nice off-white solid had turned into a brown goo on the side of the vial pointing towards the window. The initial irritation at the photochemical destruction of our main supply of the material soon gave way to curiosity, and we ultimately found that mere irradiation with a tungsten filament lamp of N -hydroxypyridine-2-thione resulted in the clean generation of hydroxyl radicals (Boivin, J.; Crépon, E.; Zard, S. Z. Tetrahedron Lett. 1990, 31, 6869). This convenient source of hydroxyl radicals was later used by various research groups to cleave DNA strands