441777-47-5Relevant academic research and scientific papers
An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclisations
Knight, David W.,Redfern, Adele L.,Gilmore, Jeremy
, p. 622 - 628 (2002)
A representative series of homopropargylic sulfonamides 19 and 22b have been found to undergo smooth 5-endo-dig cyclisation upon exposure to excess iodine in acetonitrile containing potassium carbonate. The resulting 4-iodo-2,3-dihydropyrroles 23 readily react with two equivalents of DBU in DMF at 20°C to give the corresponding β-iodopyrroles 24 and 26 in excellent yields by the elimination of toluene-p-sulfinic acid. Use of less than two equivalents of base results in some loss of iodine. The iodo-2,3-dihydropyrroles 23 can be used in palladium-catalysed coupling reactions as shown by the efficient formation of the Sonogashira product 29 under mild conditions.
Regioselectivity of larock indole synthesis using functionalized alkynes
Sugino, Kumi,Yoshimura, Hiroshi,Nishikawa, Toshio,Isobe, Minoru
, p. 2092 - 2102 (2008/12/23)
Regioselectivity of Larock indole synthesis, a palladium-catalyzed heteroannulation between o-iodoaniline and internal acetylene, was estimated using acetylenes substituted with ester and/or Boc-protected amine at the homopropargylic position and with perbenzyl- and unprotected glucose. Low to moderate regioselectivities were observed in all the cases, indicating these functional groups do not exert good directing effects, in the Larock indole synthesis.
Rhodium(I)-catalyzed cycloisomerization reaction of yne-allenamides: An approach to cyclic enamides
Brummond, Kay M.,Yan, Bingli
body text, p. 2303 - 2308 (2009/05/07)
In this paper, we demonstrate a successful conversion of alkynyl allenamides to triene-containing heterocycles via a rhodium(I)-catalyzed cycloisomerization reaction. Georg Thieme Verlag Stuttgart.
5-Endo-dig cyclisations of homopropargylic sulfonamides: A new route to 2,3-dihydropyrroles and β-iodopyrroles
Knight, David W.,Redfern, Adele L.,Gilmore, Jeremy
, p. 2207 - 2208 (2007/10/03)
5-endo-dig Iodocyclisations of the homopropargylic sulfonamides 12a-c and 13 give excellent yields of the iododihydropyrroles 14a-d and thence the β-iodopyrroles 15a-d, following base-catalysed elimination of sulfinic acid.
