81803-40-9Relevant academic research and scientific papers
Vinyl Azides in Heterocyclic Synthesis. Part 6. Synthesis of Isoquinolines by Intramolecular Aza-Wittig Reaction
Hickey, Deirdre M. B.,MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
, p. 921 - 926 (2007/10/02)
Azidocinnamates containing ortho-carbonyl substituents are versatile intermediates for heterocyclic synthesis.Isoquinolines (8) and (9) are formed under mild neutral conditions by intramolecular aza-Wittig reactions of iminophosphoranes, readily derived f
Synthesis of Isoquinolines by Intramolecular Aza-Wittig Reaction
Hickey, Deirdre M. B.,MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
, p. 776 - 777 (2007/10/02)
Isoquinolines (3) and (5) are formed under mild neutral conditions by intramolecular aza-Wittig reactions of iminophosphoranes, readily derived from azides (1) and (4) with triethyl phosphite; the azafluoranthene (7) can also be prepared from the isolable
Formation of Indoles, Isoquinolines, and Other Fused Pyridines from Azidoacrylates
Henn, Lothar,Hickey, Deirde M. B.,Moody, Christopher J.,Rees, Charles W.
, p. 2189 - 2197 (2007/10/02)
Mild thermal decomposition in boiling toluene or xylene of the azidocinnamates (1) - (6), readily prepared from the corresponding aldehyde and ethyl azidoacetate, gives indoles in good yield when there is an unsubstituted ortho position, and dihydroisoquinolines, and hence isoquinolines, when there is an o-methyl or methylene group.In the presence of iodine, which seems to favour a radical type process, the yield of isoquinoline is increased, and isoquinoline formation can compete with the indole-forming cyclisation to a free ortho-position.Iodine also catalyses primary enamine formation by a hydrogen abstraction process.The thiophene (7) and pyrazole (8) are formed and decomposed similarly to give the corresponding c-fused pyridines (28) and (29).The 2,6-dichloro compound (9) thermolyses to the stable 2H-azirine (32) which isomerises to the nitrile (33) on stronger heating.Yields in these azide decompositions are sometimes high, though they can be variable and the reactions, though easily carried out, can be complex
Synthesis of Isoquinolines from Azidocinnamates; the Effect of Iodine
Hickey, Deirdre M. B.,Moody, Christopher J.,Rees, Charles W.
, p. 3 - 4 (2007/10/02)
Iodine has a marked catalytic effect on the thermolysis of azidocinnamates; indoles, isoquinolines, 1,2-dihydroisoquinolines, or enamines are isolated depending on the conditions.
