کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5221058 | 1383407 | 2012 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes](/preview/png/5221058.png)
2-Aryl-5-acroleinyl-1,2,3,4-tetrazoles (1a-d) and 2-aryl-5-butadienyl-1,2,3,4-tetrazoles (1e-g) were subjected to flash vacuum pyrolysis. Acroleinyl derivatives resulted in nitrogen extrusion to give nitrilimines followed by ring closure to give the corresponding indazoles 3a-d in good yields. On the other hand, butadiene derivatives underwent ring fragmentation to give p-substituted anilines without formation of the expected indazoles. Differences between thermal behaviour of 2-(4-chlorophenyl)-5-acroleinyl-1,2,3,4-tetrazole (1c) and 1-(4-chlorophenyl)-4-acroleinyl-1,2,3-triazole (2) were studied in details. DFT calculations have been used to examine the nitrilimine and carbene nature of the intermediates involved in the thermal reactions of azolyl derivatives.
Journal: Tetrahedron - Volume 68, Issue 4, 28 January 2012, Pages 1299-1305