42860-69-5Relevant academic research and scientific papers
Reductive Desilanolation as a Route to Benzonitriles. An Application to a Concise Synthesis of the Aromatic Sector of Calicheamicin.
Olson, Steven H.,Danishefsky, Samuel J.
, p. 7901 - 7904 (1994)
The TMS-cyanohydrins of quinones undergo reductive desilanolation in the presence of samarium iodide to form hydroxybenzonitriles.Benzoquinone 1 was converted to the hexasubstituted aromatic fragment of calicheamicin 4 by this method.
4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines
Wells, Geoffrey,Berry, Jane M.,Bradshaw, Tracey D.,Burger, Angelika M.,Seaton, Angela,Wang, Bo,Westwell, Andrew D.,Stevens, Malcolm F. G.
, p. 532 - 541 (2007/10/03)
The synthesis and antitumor evaluation of a series of new heteroaromatic- and aromaticsubstituted hydroxycyclohexadienones ("quinols"), and their imine counterparts, are described. The quinols were synthesized via the addition of a lithiated aromatic moie
Reactions of 4-Hidroxycyclohexa-2,5-dienones under Acidic Conditions
Davis, Brian R.,Gash, Diana M.,Woodgate, Paul D.,Woodgate, Sheila D.
, p. 1499 - 1508 (2007/10/02)
The 4-hydroxy-4-phenyl-2,6-di-t-butylcyclohexa-2,5-dienone (2) undergoes reaction in acidic conditions to give, inter alia, derivatives of an arene-1,2-diol.In poorly nucleophilic media, the 1,1'-biphenyl-4-ol (16) and the 5-phenyl-o-benzoquinone (37) are the main products.Isolation of the 4-(2-methylpropyl)cyclohexadienone derivatives (41) and (42) provides the first examples of intermolecular trapping of a four-carbon unit.The products are consistent with the intervention of the phenoxenium ion (44); the formation of the 2-methyl-1,3-benzodioxole (43) testifies to the intermediacy of such a powerful oxidant.Whereas the 4- phenyl-2-t-butyl-p-quinol (5) gave a complex mixture from which only the 1,1'-biphenyl-4-ol derivative (24) was isolated, the 2,6-di-isopropyl- and 2,6-dimethyl-analogues (4) and (6) afforded mainly the arene-1,3-diol derivatives (48) and (47), respectively.The 4-methyl-2,6-di-t-butyl-p-quinol (7) gave products arising from nucleophilic attack on an intermediate p-quinone methide; dimers were the major products in the absence of a good nucleophile.
