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.

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 Efficient synthesis of dihydropyrimidinones via a three-component Biginelli-type reaction of urea, alkylaldehyde and arylaldehyde

2013 ◽  
Vol 9 ◽  
pp. 2846-2851 ◽  
Author(s):  
Haijun Qu ◽  
Xuejian Li ◽  
Fan Mo ◽  
Xufeng Lin
Keyword(s):  
Molecular Iodine ◽  
Tandem Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Reaction Proceeds ◽  
Phosphoric Acids ◽  
Substituted Urea

A one-pot three-component synthesis of dihydropyrimidinones via a molecular iodine-catalyzed tandem reaction of simple readily available mono-substituted urea, alkylaldehyde, and arylaldehyde has been developed. The reaction proceeds with high chemo- and regioselectivity to give highly diverse dihydropyrimidinones in reasonable yields under mild reaction conditions. Moreover, the first catalytic enantioselective version of this reaction was also realized by using chiral spirocyclic SPINOL-phosphoric acids.

Molecular iodine as a mild catalyst for cross-coupling of alkenes and alcohols

2018 ◽  
Vol 90 (2) ◽  
pp. 377-386 ◽  
Author(s):  
Klara Čebular ◽  
Stojan Stavber
Keyword(s):  
Molecular Diversity ◽  
Bond Formation ◽  
Cross Coupling ◽  
Acid Catalyst ◽  
Molecular Iodine ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Synthetic Procedure ◽  
Lewis Acid Catalyst ◽  
Solvent Free Reaction

Abstract C–C bond formation is one of the most fundamental approaches toward molecular diversity in organic synthesis. In pursuit of environmentally friendlier chemical approaches to organic chemistry, we present a new metal-free method for direct dehydrative cross-coupling of alcohols and alkenes using molecular iodine as a Lewis acid catalyst under solvent-free reaction conditions. The reaction is atom-economical, tolerant to air and allows simple synthetic procedure, furnishing Csp3–Csp2 coupling products with yields up to 97%. The method has proved efficient for coupling of secondary benzyl alcohols with phenyl-substituted alkenes.

Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides

2009 ◽  
Vol 2009 (10) ◽  
pp. 638-641 ◽  
Author(s):  
Xufeng Lin ◽  
Jun Wang ◽  
Fangxi Xu ◽  
Yanguang Wang
Keyword(s):  
Reaction Time ◽  
Efficient Method ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Allylic Alcohols ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Metal Free ◽  
Amidation Reaction ◽  
Operational Simplicity

A highly efficient method for the C–N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allylic amides in moderate to excellent yields. The significan features of the procedure include mild and metal-free reaction conditions, operational simplicity, inexpensive reagents, short reaction time, and good yields.

Molecular Iodine-Catalyzed Carbonyl-Olefin Metathesis

2018 ◽  
Author(s):  
Thanh Vinh Nguyen ◽  
Uyen P. N. Tran ◽  
Giulia Oss ◽  
Martin Breugst ◽  
Eric Detmar ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Molecular Iodine ◽  
Mechanistic Studies ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Elemental Iodine

The carbonyl-olefin metathesis reaction is a synthetically valuable transformation that could facilitate rapid functional group interconversion and construction of new organic structures. Herein we demonstrate that elemental iodine, a very simple and mild catalyst, can efficiently promote this chemical transformation under mild reaction conditions with excellent outcomes. Our mechanistic studies revealed intriguing aspects of iodine activation mode that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.

Highly selective mono-N-benzylation and amidation of amines with alcohols or carboxylic acids using the Ph2PCl/I2/imidazole reagent system

2012 ◽  
Vol 90 (6) ◽  
pp. 498-509 ◽  
Author(s):  
Najmeh Nowrouzi ◽  
Mohammad Zareh Jonaghani
Keyword(s):  
Carboxylic Acids ◽  
Molecular Iodine ◽  
Basic Solution ◽  
Reaction Conditions ◽  
Chromatographic Methods ◽  
Excellent Selectivity

Chlorodiphenylphosphine, imidazole, and molecular iodine in refluxing dichloromethane are used for the efficient preparation of amides under mild reaction conditions. This reagent system also shows excellent selectivity for mono-N-alkylation of amines with alcohols. In this system, the resulting phosphorus byproduct (diphenylphosphinic acid) is easily removed by extraction using an aqueous basic solution in the workup processes, which avoids the tedious and time-consuming chromatographic methods.

scholarly journals Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines

2014 ◽  
Vol 10 ◽  
pp. 2065-2070 ◽  
Author(s):  
Praveen Reddy Adiyala ◽  
D Chandrasekhar ◽  
Jeevak Sopanrao Kapure ◽  
Chada Narsimha Reddy ◽  
Ram Awatar Maurya
Keyword(s):  
Environmental Impact ◽  
Coupling Reaction ◽  
Molecular Iodine ◽  
Atom Economy ◽  
Reaction Conditions ◽  
High Yields ◽  
Three Component Coupling

A facile and efficient synthetic protocol for the synthesis of α-amino amidines has been developed using a molecular iodine-catalyzed three-component coupling reaction of isocyanides, amines, and aldehydes. The presented strategy offers the advantages of mild reaction conditions, low environmental impact, clean and simple methodology, high atom economy, wide substrate scope and high yields.

Synthesis of 3-Halo-7-azaindoles through a 5-endo-dig Electrophilic Cyclization Reaction

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1246-1252 ◽  
Author(s):  
Aimee Philips ◽  
Christopher Cunningham ◽  
Kajal Naran ◽  
Tanay Kesharwani
Keyword(s):  
Sodium Chloride ◽  
Molecular Iodine ◽  
Cyclization Reaction ◽  
Sodium Bromide ◽  
Environmentally Benign ◽  
Electrophilic Cyclization ◽  
Reaction Conditions ◽  
High Yields ◽  
Simple Atom

Biologically useful 7-azaindoles were synthesized by electrophilic cyclization of 3-alkynyl-N,N-dimethylpyridine-2-amines with molecular iodine. By this simple atom-economical approach under ambient reaction conditions, a library of interesting 3-iodo-7-azaindoles were synthesized in high yields. To synthesize the corresponding 3-bromo- and 3-chloro-7-azaindoles, an environmentally benign copper-mediated cyclization was employed, with inexpensive, nontoxic, and noncorrosive sodium chloride and sodium bromide as the sources of chlorine and bromine, respectively.

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.

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