English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Titanium-Induced Syntheses of Furans, Benzofurans and lndoles

MPS-Authors
There are no MPG-Authors available
Locator
There are no locators available
Fulltext (public)
There are no public fulltexts available
Supplementary Material (public)
There is no public supplementary material available
Citation

Fürstner, A., & Jumbam, D. N. (1992). Titanium-Induced Syntheses of Furans, Benzofurans and lndoles. Tetrahedron, 48(29), 5991-6010. doi:10.1016/S0040-4020(01)89848-3.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A4C4-D
Abstract
Highly reactive titanium on graphite as the reagent of choice promotes intramolecular McMurry-type reactions of acyloxy and acylamido carbonyl compounds affording furans, benzofurans and indoles in good to excellent yields. A variety of reducible groups in the substrates is tolerated (e.g. -F, -Cl, -Br, -I, -CF3, -OMe, -CN, -thiophenyl, -COOR, -CONR2 and strained products such as I can be obtained (by reductive cyclization of acylanilide II), the x-ray analysis of which is reported. The experimental results indicate the possible formation of dianions from the aromatic aldehydes or ketones as reactive intermediates which attack the ester or amide functions in their proximity, rather than a radical path via ketyls.