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.

Transition-metal-free arylation of benzoxazoles with aryl nitriles

2018 ◽  
Vol 5 (11) ◽  
pp. 1811-1814 ◽  
Author(s):  
Aizhen Wu ◽  
Quan Chen ◽  
Wei Liu ◽  
Lijun You ◽  
Yifan Fu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Reaction Conditions ◽  
Metal Free ◽  
Simple Reaction ◽  
Aryl Nitriles

Transition-metal-free arylation of benzoxazoles with aryl nitriles has been developed to afford important 2-aryl benzoxazoles under simple reaction conditions.

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.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

2020 ◽  
Vol 44 (5-6) ◽  
pp. 301-304
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Ruoqi Yang ◽  
Fengzhe Guo ◽  
Zi-Long Tang ◽  
...  
Keyword(s):  
Aromatic Acid ◽  
Aliphatic Acid ◽  
Acid Chlorides ◽  
Alkyl Esters ◽  
Reaction Conditions ◽  
Simple Reaction ◽  
Tert Butyl ◽  
Butyl Esters ◽  
Plausible Mechanism ◽  
First Time

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

Simple Reaction Conditions for the Formation of Ketonitrones from Ketones and Hydroxylamines

2009 ◽  
Vol 74 (21) ◽  
pp. 8381-8383 ◽  
Author(s):  
Jennifer Y. Pfeiffer ◽  
André M. Beauchemin
Keyword(s):  
Reaction Conditions ◽  
Simple Reaction

One pot oxidative N–S bond formation to access 2-sulfenylimine chromenes

2016 ◽  
Vol 14 (2) ◽  
pp. 582-589 ◽  
Author(s):  
Ashok Kale ◽  
Madhu Chennapuram ◽  
Chiranjeevi Bingi ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnaiah Atmakur
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
One Pot ◽  
Simple Reaction ◽  
Catalyst Free

Synthesis of 2-sulfenylimine chromene compounds is accomplished in a one-pot, catalyst-free, five-component reaction in toluene. When aniline was employed as nucleophile formation of hexahydrobenzofuran-2-N-phenyl carboxamide was observed. Excellent yields, simple reaction conditions high compatibility are the advantages of this protocol.

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.

scholarly journals Regioselective Asymmetric Alkynylation of N–Alkyl Pyridiniums

2021 ◽  
Author(s):  
Thiago A. Grigolo ◽  
Ariana R. Subhit ◽  
Joel Smith
Keyword(s):  
Asymmetric Synthesis ◽  
Acetylcholine Esterase ◽  
Reaction Conditions ◽  
Asymmetric Addition ◽  
Simple Reaction ◽  
Stereochemical Control ◽  
Acetylcholine Esterase Inhibitor ◽  
Esterase Inhibitor

Disclosed in this communication is a novel asymmetric addition of alkynyl nucleophiles to <i>N</i>-alkyl pyridinium electrophiles. The coupling is effected under mild and simple reaction conditions, affording dihydropyridine products with complete regiochemical and stereochemical control. In addition to several manipulations of the dihyropyridine products, the utility of this transformation is demonstrated through a concise, dearomative, and asymmetric synthesis of (+)-lupinine, a natural acetylcholine esterase inhibitor.

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