135484-76-3Relevant articles and documents
Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes
Chu, John C. K.,Dalton, Derek M.,Rovis, Tomislav
supporting information, p. 4445 - 4452 (2015/04/14)
We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due to limiting the undesired coordination of 1-azadiene to the Lewis acid and thus allowing the reaction to be carried out at lower temperature. A series of secondary kinetic isotope effect studies using a range of ligands implicates a stepwise mechanism for the transformation, involving an initial Michael-type addition of the imine to the nitro-alkene followed by a cyclization event. The stepwise mechanism obviates the electronic requirement inherent to a concerted mechanism, explaining the successful cycloaddition between two electron-deficient partners. (Chemical Equation Presented).
A microwave-assisted alternative synthesis of 8-amino-2-methyl-3,4- dihydroisoquinolin-1-one
Glossop, Steve C.
, p. 981 - 983 (2008/02/02)
A shorter, alternative synthesis of 8-amino-2-methyl-3,4- dihydroisoquinolin-1-one is described in 32% overall yield, over three steps starting from commercially available 2-methyl-6-nitrobenzonitrile. The synthesis includes two 'one-pot' procedures in wh
PYRIMIDINE DERIVATIVES
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Page/Page column 80; 81, (2008/06/13)
Novel pyrimidine derivatives of formula (I) to processes for their production, their use as pharmaceuticals and to pharmaceutical compositions comprising them.
Acid-catalysed Cyclisation of o-Sulphonamido Ketene Dithioacetal S-Oxides: A Novel Synthesis of the Indole Ring System
Hewson, Alan T.,Hughes, Kevin,Richardson, Steward K.,Sharpe, David A.,Wadsworth, Alan H.
, p. 1565 - 1569 (2007/10/02)
Treatment of o-sulphonamido aryl ketene dithioacetal S-oxides with hydrochloric acid in the presence of hydrogen sulphide gives 2-methylthioindoles.