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3. Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst

Author

Prajwal Balgi, Kumaresan Vignesh, Viswanadhan Abhilash, Sambasivam Ganesh, A. M. Sathiyanarayanan, Amol V. Gadakh, Atul K. Godha, Jayaraman Thiruvengadam, and A. V. Narayanareddy

Subjects
Quinoline, Inverse, Halide, Regioselectivity, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, Highly selective, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Materials Chemistry, Nucleophilic substitution, Methylene, 0210 nano-technology, Phase-transfer catalyst
Abstract

An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.

Published
2019

5. Hetero Diels-Alder reaction of olefin with o-quinone methides generated using (�)-binolphosphoric acid for the stereoselective synthesis of 2,4-diarylbenzopyrans: Application to the formal synthesis of myristinin B/C

Author

Santosh J. Gharpure, A. M. Sathiyanarayanan, and Prasanna K. Vuram

Subjects
Biomimetic Synthesis, Alkylation, Stereochemistry, General Chemical Engineering, O quinones, Olefins, Formal synthesis, Hydroxybenzyl Alcohols, Phenols, Organic chemistry, In-Situ, Myristinin B, Hetero Diels-Alder reaction, Quinonemethides, Diels–Alder reaction, Construction, Olefin fiber, Chemistry, Inhibitors, Stereoselective synthesis, Stereoselectivity, General Chemistry, O-quinone methides, Cyclization, Vinylogous Carbonates, Polyols
Abstract

Hetero Diels-Alder reaction of olefin with o-quinone methides (o-QMs) generated using (�)-binolphosphoric acid was developed for the stereoselective synthesis of 2,4-diarylbenzopyrans. The method thus developed was utilized in the formal synthesis of myristinin B/C. � 2013 The Royal Society of Chemistry.

Published
2013
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6. ChemInform Abstract: Stereoselective Synthesis of Oxazino[4,3-a]indoles Employing the Oxa-Pictet-Spengler Reaction of Indoles Bearing N-Tethered Vinylogous Carbonate

Author

A. M. Sathiyanarayanan and Santosh J. Gharpure

Subjects
chemistry.chemical_compound, Pictet–Spengler reaction, chemistry, Carbonate, Stereoselectivity, General Medicine, Medicinal chemistry
Abstract

A novel strategy for the stereoselective synthesis of N-fused oxazinoindoles (II) and (IV) employing a TmsOTf mediated oxa-Pictet—Spengler reaction of vinylogous carbonates (I) and (III).

Published
2011

7. Stereoselective synthesis of oxazino[4,3-a]indoles employing the oxa-Pictet-Spengler reaction of indoles bearing N-tethered vinylogous carbonate

Author

A. M. Sathiyanarayanan and Santosh J. Gharpure

Subjects
Bearing (mechanical), Pictet–Spengler reaction, Indoles, Chemistry, Stereochemistry, Nitrogen, carbonic acid, indole derivative, oxazino[4,3 a]indole derivative, unclassified drug, chemical reaction, cyclization, one pot synthesis, oxa Pictet Spengler reaction, stereochemistry, substitution reaction, Carbonates, Oxidation-Reduction, Stereoisomerism, Substrate Specificity, Metals and Alloys, General Chemistry, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, law.invention, Electrophilic substitution, chemistry.chemical_compound, law, Intramolecular force, Materials Chemistry, Ceramics and Composites, Carbonate, Stereoselectivity
Abstract

A one-pot, sequential 2,3-bis-functionalization of indoles bearing N-tethered vinylogous carbonates employing an intramolecular oxa-Pictet-Spengler reaction followed by electrophilic substitution is developed for the stereoselective synthesis of oxazino[4,3-a]indoles. � 2011 The Royal Society of Chemistry.

Published
2011

8. ChemInform Abstract: o-Quinone Methide Based Approach to Isoflavans: Application to the Total Syntheses of Equol, 3′-Hydroxyequol and Vestitol

Author

Prasad Jonnalagadda, A. M. Sathiyanarayanan, and Santosh J. Gharpure

Subjects
chemistry.chemical_compound, Chemistry, Stereochemistry, Reductive cleavage, Acetal, General Medicine, Equol, O quinones, Enol
Abstract

A concise strategy is developed for the synthesis of isoflavans employing a Diels–Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.

Published
2008

9. o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3?-hydroxyequol and vestitol

Author

A. M. Sathiyanarayanan, Prasad Jonnalagadda, and Santosh J. Gharpure

Subjects
2 quinone methide, 3' hydroxyequol, equol, isoflavan derivative, quinone derivative, unclassified drug, vestitol, chemical stress, Diels Alder reaction, gel chromatography, synthesis, Alnus, Stereochemistry, Organic Chemistry, Acetal, Equol, O quinones, Biochemistry, Enol, chemistry.chemical_compound, chemistry, Reductive cleavage, Drug Discovery, Organic chemistry, Diels–Alder reaction
Abstract

A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3?-hydroxyequol and vestitol. � 2008 Elsevier Ltd. All rights reserved.

Published
2008
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