1260841-18-6Relevant articles and documents
Flash vacuum thermolysis of N-(3-and 4-Pyridylmethylidene)-tert- butylamines: Mechanisms of formation of pyrrolopyridines and naphthyridines
Justyna, Katarzyna,Lesniak, Stanislaw,Nazarski, Ryszard B.,Rachwalski, Michal,Vu, Thien Y.,Huynh, Thi Kieu Xuan,Khayar, Said,Dargelos, Alain,Chrostowska, Anna,Wentrup, Curt
supporting information, p. 3020 - 3027 (2014/05/20)
Pyrrolopyridines and naphthyridines are formed by flash vacuum thermolysis (FVT) of 3-and 4-pyridylmethylidene-tert-butylimines 8 and 15. Elimination of a methyl radical generates resonance stablized 2-azaallyl radicals a1 and b1. The formation of pyrrolopyridines 9, 16 and 17 is rationalized in terms of cyclization of 1-aziridinyl radicals a2 and b2. Formation of naphthyridine 10 from imine 8, and of 11 and 18 from imine 15, are in accord with cyclization of 1-azaallyl radicals a6 and b9. Formation of naphthyridine 11 from 8, and of 10 and 19 from 15, indicate the operation of the spiro-cyclization pathways forming intermediates a9 and b14. Formation of the 1,8-naphthyridine 20 (3%) indicates a rearrangement through aziridine b22 and biradical b23. DFT calculations at the CAM-B3LYP/6-311G(d,p) level support the proposed reaction mechanisms.
