| Автор | Reisinger, Ales |
| Автор | Bernhardt, Paul V. |
| Автор | Wentrup, Curt |
| Дата выпуска | 2004 |
| dc.description | Several tetrazolo[1,5-a]pyridines/2-azidopyridines undergo photochemical nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4,6-tetraenes (7,10,13,16,19,22) as well as ring cleavage to cyanovinylketenimines (8,17,20b) in low temperature Ar matrices. 6,8-Dichlorotetrazolo[1,5-a]pyridine/2-azido-3,5-dichloropridine 6 undergoes ready exchange of the chlorine in position 8 (3) with ROH/RONa. 8-Chloro-6-trifluoromethyltetrazolo[1,5-a]pyridine 15 undergoes solvolysis of the CF3 group to afford 8-chloro-6-methoxycarbonyltetrazolo[1,5-a]pyridine 18. Several tetrazolopyridines/2-azidopyridines afford 1H- or 5H-1,3-diazepines in good yields on photolysis in the presence of alcohols or amines (11,14,23,25). 5-Chlorotetrazolo[1,5-a]pyridines/2-azido-6-chloropyridines 21 and 38 undergo a rearrangement to 1H- and 3H-3-cyanopyrroles 27 and 45, respectively. The mechanism of this rearrangement was investigated by <sup>15</sup>N-labelling and takes place via transient 1,3-diazepines. The structures of 6,8-dichloro-tetrazolo[1,5-a]pyridine 6T, 6-chloro-8-ethoxytetrazolo[1,5-a]pyridine 9Tb, dipyrrolylmethane 28, and 2-isopropoxy-4-dimethylamino-5H-1,3-diazepine 25b were determined by X-ray crystallography. In the latter case, this represents the first reported X-ray crystal structure of a 5H-1,3-diazepine. |
| Формат | application.pdf |
| Издатель | Royal Society of Chemistry |
| Название | Synthesis of 1,3-diazepines and ring contraction to cyanopyrrolesDiazepines. Part 2. For Part 1 see ref. 1.Electronic supplementary information (ESI) available: drawings of the crystal structures of compounds 6T and 9Tb (ORTEP); bond lengths and angles for compounds 6T, 9Tb, 25h and 28, and 15N NMR spectra of 21, 30, 27 and 37. See http://www.rsc.org/suppdata/ob/b3/b311247k/ |
| Тип | research-article |
| DOI | 10.1039/b311247k |
| Electronic ISSN | 1477-0539 |
| Print ISSN | 1477-0520 |
| Журнал | Organic & Biomolecular Chemistry |
| Том | 2 |
| Первая страница | 246 |
| Последняя страница | 256 |
| Аффилиация | Reisinger Ales; Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland |
| Аффилиация | Bernhardt Paul V.; Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland |
| Аффилиация | Wentrup Curt; Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland |
| Выпуск | 2 |
| Библиографическая ссылка | A. Reisinger, R. Koch, C. Wentrup, Part 1: , J. Chem. Soc., Perkin Trans. 1, 1998, 2247 |
| Библиографическая ссылка | A. Reisinger, C. Wentrup, Chem. Commun., 1996, 813 |
| Библиографическая ссылка | R. A. Evans, M. W. Wong, C. Wentrup, C. Wentrup, H.-W. Winter, J. Am. Chem. Soc., 1996, 118, 4009, J. Am. Chem. Soc., 1980, 102, 6159 |
| Библиографическая ссылка | O. L. Chapman, Pure Appl. Chem., 1979, 51, 331 |
| Библиографическая ссылка | C. Addicott, A. Reisinger, C. Wentrup, J. Org. Chem., 2003, 68, 1470 |
| Библиографическая ссылка | U. H. Patel, C. G. Dave, M. M. Jotani, H. C. Shah, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2002, 58, o431 |
| Библиографическая ссылка | D. Donati, S. Fusi, F. Ponticelli, J. Chem. Res., Synop., 1997, 170 |
| Библиографическая ссылка | P. Molina, A. Arques, A. Alias, M. C. Foces-Foces, A. L. Llamas-Saiz, J. C. Teulade, A. Gueiffier, J. P. Chapat, G. Grassy, A. Carpy, A. H'Naifi, B. Perly, J. Couquelet, J. Chem. Soc., Chem. Commun., 1992, 424, Chem. Pharm. Bull., 1989, 37, 2293 |
| Библиографическая ссылка | D. A. Lightner, A. K. Tipton, D. A. Lightner, Monatsh. Chem., 2000, 131, 451 |
| Библиографическая ссылка | T. Mukai, T. Kumagai, Y. Yamashita, Heterocycles, 1981, 15, 1569 |
| Библиографическая ссылка | A. Kuhn, C. Plüg, C. Wentrup, J. Am. Chem. Soc., 2000, 122, 1945 |
| Библиографическая ссылка | L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837 |
| Библиографическая ссылка | L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565 |
| Библиографическая ссылка | C. D. Nenitzescu, E. Solomonics, Org. Synth., Coll. Vol. II, 1943, 496 |
