797799-58-7Relevant articles and documents
Masked mercapto acid-driven MCR in task-specific ionic liquid: A new sterocontrolled entry into bicyclic 1,3-thiazines
Rai, Vijai K.,Rai, Prashant Kumar,Thakur, Yogita
, p. 6469 - 6473 (2013)
An unprecedented multi-component reaction for the synthesis of thiosugar-annulated 1,3-thiazines is reported. The envisaged synthetic strategy involves the reaction of d-glucose/d-xylose and 2-methyl-2-phenyl-1,3- oxathiolan-5-one with AcONH4/RNH2 in task specific ionic liquid (TSIL), [bmim]SCN which afforded thiosugar annulated 1,3-thiazines in excellent yields (83-93%). The reaction is effected via ionic liquid promoted Michael addition followed by mercaptoacetylative ring transformation in a one-pot procedure and the ionic liquid, [bmim]OH could be easily recycled for further use without any loss of efficiency and be used for the synthesis of [bmim]SCN, thus allowing recycling of the TSIL for further use.
The first regio- and diastereoselective direct introduction of α-mercaptoacetic acid/amide units into Morita-Baylis-Hillman acetates
Yadav, Lal Dhar S.,Rai, Viaji K.
, p. 2414 - 2419 (2009)
The exposure of Morita-Baylis-Hillman acetates to mercaptoacetyl transfer agent, 2-methyl-2-phenyl-1,3-oxathiolan-5-one, in the presence of 1,4-diazabicyclo[2.2.2]octane enables the regio- and stereoselective allylic substitution through a tandem SN
Catalyst-free, step and pot economic, efficient mercaptoacetylative cyclisation in H2O: Synthesis of 3-mercaptocoumarins
Yadav, Lal Dhar S.,Singh, Santosh,Rai, Vijai K.
, p. 878 - 882 (2009)
A novel, environmentally friendly, tandem Knoevenagel condensation and mercaptoacetylative cyclisation procedure is reported. The reaction between 2-methyl-2-phenyl-1,3-oxathiolan-5-one and a variety of salicylaldehydes was carried out in water to afford
One-pot cis -selective route to sugar-fused thiazines via a masking-unmasking strategy in basic ionic liquid
Rai, Vijai K.,Kosta, Rahul K.
, p. 827 - 832 (2016)
A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, d-xylose/d-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim]OH. The acetophenone obtained as a by-product and [bmim]OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.
Mercaptoacetic acid based expeditious synthesis of polyfunctionalised 1,3-thiazines
Yadav, Lal Dhar S.,Yadav, Seema,Rai, Vijai K.
, p. 10013 - 10017 (2005)
A novel three-component expeditious synthesis of 3,6-diaryl-5- mercaptoperhydro-2-thioxo-1,3-thiazin-5-ones from 2-methyl-2-phenyl-1,3- oxathiolan-5-one, an aromatic aldehyde and an N-aryldithiocarbamic acid is reported. The synthesis is diastereoselective and involves tandem Knoevenagel, Michael and ring transformation reactions under solvent-free microwave irradiation in a one-pot procedure.
Efficient Ce(III)-catalyzed cis-selective synthetic approach to γ-lactones in aqueous media
Rai, Vijai K.,Tiku, Priya,Kumar, Anil
scheme or table, p. 1489 - 1499 (2012/04/17)
The first CeCl3 ·7H2O-catalyzed. one-pot synthesis of α-mercapto-γ -lactones via regioselective epoxide ring opening and mercaptoacetylative cyclization cascades in water is reported. The reaction between 2-methyl-2-phenyl-1,3-oxathiolan-5-one and a variety of terminal epoxides was carried out in aqueous media to afford γ-lactones in good to excellent yields (83-94%) with complete cis diastereoselectivity. Acetophenone obtained as a by-product was also recovered and recycled easily for further use. Copyright Taylor & Francis Group, LLC.
An unprecedented synthesis of γ-lactams via mercaptoacetylation of aziridines in water
Rai, Vijai K.,Rai, Prashant Kumar,Bajaj, Swati,Kumar, Anil
scheme or table, p. 1217 - 1223 (2011/06/26)
A highly green and expeditious route to α-mercapto-γ-lactams from masked mercapto acids viz. 2-phenyl-2-methyl-1,3-oxathiolan-5-ones, and tosyl aziridines in an excellent yield (82-93%) is reported. The synthetic protocol involves regioselective opening of the terminal aziridine ring and mercaptoacetylative cyclisation cascades in a one-pot procedure wherein water acts as both a catalyst as well as a solvent. These reactions were carried out in aqueous media as well as under solvent-free conditions, however, under solvent-free conditions, lower yields are obtained.
