Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

2016 ◽  
Vol 14 (22) ◽  
pp. 5073-5078 ◽  
Author(s):  
Sadhanendu Samanta ◽  
Sourav Jana ◽  
Susmita Mondal ◽  
Kamarul Monir ◽  
Swapan K. Chandra ◽  
...  
Keyword(s):  
Molecular Iodine ◽  
Regioselective Synthesis ◽  
Reaction Conditions ◽  
Aerobic Reaction

A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkenes/alkynes as coupling partners in the presence of molecular iodine under aerobic reaction conditions.

Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles

2017 ◽  
Vol 41 (1) ◽  
pp. 75-80 ◽  
Author(s):  
Sethurajan Ambethkar ◽  
Muthalu Vellimalai ◽  
Vediappen Padmini ◽  
Nattamai Bhuvanesh
Keyword(s):  
Reaction Time ◽  
Intramolecular Cyclization ◽  
Simple Procedure ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Regioselective Synthesis ◽  
Thiazole Derivatives ◽  
Short Reaction Time ◽  
Metal Free

The regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives via amination (C–N) and intramolecular cyclization (C–S) reactions in the presence of molecular iodine has been reported. This method is base and metal free and features inexpensive catalysts, with a simple procedure and a short reaction time.

scholarly journals High Yielding, Base Catalyzed C6 Regioselective Amination and N9 Alkylation in Purine Nucleotide

2019 ◽  
Vol 31 (12) ◽  
pp. 2871-2874
Author(s):  
Gautamkumar Dhuda ◽  
Khushal Kapadiya ◽  
Paresh Ladwa ◽  
Bhavna Godhaniya ◽  
Jayesh Modha
Keyword(s):  
Coupling Reaction ◽  
Purine Nucleoside ◽  
Regioselective Synthesis ◽  
Secondary Amines ◽  
Purine Nucleotide ◽  
Reaction Conditions ◽  
Simple Reaction ◽  
Amine Coupling

2,6-Dichloropurine is an interesting new nucleoside which gave regioselectively various 2-derivatized or 6-derivatized purines by using a secondary amines. An efficient, simple and regioselective synthesis of C6 morpholine, N9 alkylated purine nucleoside derivatives were attained via chloro-amine coupling reaction between 2,6-dichloropurine with morpholine followed by commercial alkylation method using DMF and K2CO3. Over the traditionally used protocols and procedure, it have been exhibited advance benefits such as admirable yield, simple reaction conditions and modest influence.

Diiodine–Triethylsilane System: Reduction of N-Sulfonyl Aldimines to N-Alkylsulfonamides

Synlett ◽  
2020 ◽  
Author(s):  
Jin Jiang ◽  
Lili Xiao ◽  
Yu-Long Li
Keyword(s):  
Practical Method ◽  
Molecular Iodine ◽  
Reaction Conditions ◽  
System Reduction

AbstractBecause molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N-sulfonyl aldimines to the corresponding N-alkylsulfonamides. This transformation is a practical method for the synthesis of N-alkylsulfonamides.

Molecular-Iodine-Promoted Synthesis of Dihydrobenzofuran-3,3-dicarbonitriles through a Novel Rearrangement

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 293-298
Author(s):  
Nagaraju Medishetti ◽  
Ashok Kale ◽  
Jagadeesh Nanubolu ◽  
Krishnaiah Atmakur
Keyword(s):  
Molecular Iodine ◽  
Basic Medium ◽  
Reaction Conditions ◽  
Simple Reaction

The title compounds were synthesized from 5,5-dimethyl­cyclohexane-1,3-dione, benzaldehyde, and malononitrile promoted by molecular iodine in basic medium via 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, by a novel protocol. The protocol involves a novel rearrangement in which the 4H-chromene fragment dissociates to a cyclopropane moiety and rearranges to the five-membered compound 6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran-3,3(2H)-dicarbonitrile. Simple reaction conditions, excellent yields, and high compatibility are the advantages of this protocol.

scholarly journals Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction

2020 ◽  
Vol 44 (9-10) ◽  
pp. 592-597
Author(s):  
Lin Jiang ◽  
Wen-Fei Jin ◽  
Liu-Dong Yu ◽  
Ming-Wei Yuan ◽  
Hong-Li Li ◽  
...  
Keyword(s):  
Environmentally Friendly ◽  
Regioselective Synthesis ◽  
Reaction Conditions ◽  
Unsaturated Aldehydes ◽  
High Yields ◽  
Environmentally Friendly Method

A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α,β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.

Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines

2017 ◽  
Vol 15 (21) ◽  
pp. 4686-4696 ◽  
Author(s):  
Sonu Kumar ◽  
Mohammad Mujahid ◽  
Akhilesh K. Verma
Keyword(s):  
Molecular Iodine ◽  
Reaction Conditions

A tandem approach for the synthesis of iodo benzo[a]phenazine derivatives using molecular iodine has been described under mild reaction conditions.

Molecular Iodine Mediated Regioselective Synthesis of Pyranocoumarins and Bis-Fused Benzo-2H-pyran Derivatives

Synthesis ◽  
2014 ◽  
Vol 46 (13) ◽  
pp. 1807-1814 ◽  
Author(s):  
K. Majumdar ◽  
Biswajit Sinha ◽  
Inul Ansary ◽  
Sintu Ganai ◽  
Debankan Ghosh ◽  
...  
Keyword(s):  
Molecular Iodine ◽  
Regioselective Synthesis

DABCO Promoted Regioselective Synthesis of New Diversely Functionalized 3-Hydroxy-2-Oxindole Scaffolds

2014 ◽  
Vol 67 (5) ◽  
pp. 768 ◽  
Author(s):  
Pramod B. Thakur ◽  
Jagdeesh B. Nanubolu ◽  
Harshadas M. Meshram
Keyword(s):  
Catalytic Amount ◽  
Regioselective Synthesis ◽  
Reaction Conditions ◽  
Metal Free ◽  
Structural Framework

An efficient and highly regioselective γ-addition of β-keto sulfones on isatins has been achieved in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) to afford a γ-(3-hydroxy-2-oxindole)-β-keto sulfone structural framework. The scope of the method is tested by screening a series of isatin electrophiles as well as β-keto sulfones. The described method was found to be very handy and provides straightforward access for the diversely functionalized 3-β-keto sulfone substituted-3-hydroxy-2-oxindole structural scaffolds in very good yields from readily available starting materials under metal-free reaction conditions.

Regioselective synthesis of pyridoquinolones and pyridocoumarins via molecular iodine-mediated 6-endo-dig electrophilic cylization

2011 ◽  
Vol 52 (3) ◽  
pp. 411-414 ◽  
Author(s):  
K.C. Majumdar ◽  
Inul Ansary ◽  
Srikanta Samanta ◽  
Brindaban Roy
Keyword(s):  
Molecular Iodine ◽  
Regioselective Synthesis
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