Detail of "2644-93-1"

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Formation of indoles, isoquinolines, and other fused pyridines from azidoacrylates

Formation of indoles, isoquinolines, and other fused pyridines from azidoacrylates. Henn, Lothar; Hickey, Deirdre M. B.; Moody, Christopher J.; Rees, Charles W. (Dep. Chem., Imp. Coll. Sci. Technol., London SW7 2AY, UK). J. Chem. Soc., Perkin Trans. 1, (9), 2189-96 (English) 1984.Several substances like 2644-93-1 may be metioned in this study. CODEN: JCPRB4. ISSN: 0300-922X. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 22, 25, 28 RCH:C(CO2Et)N3 (I; R = 2,4,6-Me3C6H2, 2-PhCH2C6H4, 2-PhCH2OC6H4, fluoren-1-yl, 2-MeC6H4, 2-Me2CHC6H4), prepd. from RCHO and EtO2CCH2N3, underwent mild thermal decompn. in boiling PhMe or Me2C6H4 to give indoles in good yield when there is an unsubstituted ortho position, and dihydroisoquinolines, and hence isoquinolines, when there is an o-Me or methylene group. In the presence of iodine, which favors a radical type process, the yield of isoquinoline is increased, and isoquinoline formation competes with the indole-forming cyclization to a free ortho position. Iodine also catalyzed primary enamine formation by H abstraction. Similar decompn. of I (R = 3-methyl-2-thienyl, 1,3,5-trimethylpyrazol-4-yl), prepd. analogously from RCHO and EtO2CCH2N3, gave the fused pyridines II and III, resp. I (R = 2,6-Cl2C6H3) thermolyzed to the azirine IV which isomerized to 2,6-Cl2C6H3CH(CO2Et)CN on stronger heating. .