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Heteroannulation of nitroketene N,S-arylaminoacetals with POCl3: a novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines.
[reaction: see text]. A novel regioselective route for the synthesis of substituted and fused 3-chloro-2-(methylthio)quinoxalines through POCl3-mediated heteroannulation of a range of
Regio- and chemoselective metalation of arenes and heteroarenes using hindered metal amide bases.
TLDR
These TMP(n)MX(m)⋅p LiCl reagents are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis.
Cyclocondensation of Hydroxylamine with 1,3‐Bis(het)arylmonothio 1,3‐Diketones and 1,3‐Bis(het)aryl‐3‐(methylthio)‐2‐prop­enones: Synthesis of 3,5‐Bis(het)arylisoxazoles with Complementary
Efficient routes for the regioselective synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine
4-Alkoxy-3-cyano-2(1H)-pyridones and 5-Alkoxyisoxazoles and Their Aryl Substituted and Annulated Derivatives from Acylketene O,S-Acetals
The title pyridones 2 and 5 and the isoxazoles 3 are obtained in moderate to good yields by cyclocondensation of the appropriate acylketene O,S-acetals 1 or 4 with cyanoacetamide and hydroxylamine
An expeditious synthesis of substituted and annelated pyrido[2,3-b]indoles
An efficient and versatile synthesis of substituted and annelated pyrido[2,3-b]indoles (α-carboline) involving conjugate displacement on α-oxoketene dithioacetals by 1-methyl-2-oxoindole enolate
Studies on regioselective addition of benzylic organometallics to α-oxoketene dithioacetals in our aromatic annelation protocol
Abstract The α-oxoketene dithioacetals derived from various acyclic and cyclic active methylene ketones are shown to undergo either 1,2- or sequential 1,4- and 1,2-addition with various substituted
Enantioselective palladium-catalyzed transformations.
An efficient highly regioselective synthesis of 2,3,4-trisubstituted pyrroles by cycloaddition of polarized ketene S,S- and N,S-acetals with activated methylene isocyanides.
TLDR
An efficient route for regioselective synthesis of 2,3,4- substituted pyrroles allowing precise control over the introduction of a number of substituents and functionalities at the three positions of the pyrrole ring has been developed via 1,3-dipolar cycloaddition of readily accessible polarized ketene S, S- and N,S-acetals with carbanions derived from activated methylene isocyanides.
One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2 + 2 + 1] Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones, α-Substituted Methylamines and Sodium Nitrite through α-Nitrosation of
TLDR
This novel sequential one-pot, three step protocol, wherein three new carbon nitrogen bonds are formed in contiguous fashion, involves in situ generation of enaminones by reaction of monothio-1,3-diketones with α-substituted methylamines followed by their α-nitrosation with sodium nitrite and subsequent base mediated intramolecular heterocyclization.
Attempted Simmon–Smith reaction on β-alkylthio-α,β-unsaturated ketones: a regiospecific synthesis of 2,4-disubstituted thiophenes
A new regiospecific route to 2,4-disubstituted thiophenes has been developed through Simmon–Smith reaction on β-methylthio-α,β-unsaturated ketones. Extension of the reaction to
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