Sulfones have been attractive targets for synthetic organic chemists owing to their immense applications in medicinal, material, and chemistry. In this context, an efficient transition-metal-free process has demonstrated, wherein a broad range of alkyl/aryl/heteroaryl sodium sulfinates react with varyingly substituted aryne precursors (o-silyl aryl triflates) under mild reaction conditions afford structurally diverse sulfones good excellent yields.

A new 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based probe molecule (L) is synthesized for specific binding to Hg2+ ion in physiological condition with an associated luminescence ON response the near-IR region of spectrum. Appropriate functionalization 5-position each two pyrrole moieties styryl functionality a BODIPY core helped us achieving extended conjugation and facile intramolecular charge transfer transition narrow energy gap frontier orbitals. This accounted poor emission...

Synthesis of organo-phosphorus compounds and their application in organic synthesis life sciences has been a topic contemporary interest. Michaelis–Arbuzov reaction is the most extensively utilized method for preparation, which works well only with aliphatic halides. Hence, relatively harsh conditions using transition-metal-catalyzed P-arylation (Arbuzov/Hirao reaction) are used preparation aryl-phosphorus compounds. Presented herein competent process aryl-phosphonates, -phosphinates,...

The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, transformation follows mechanism involving pathway. scope generality developed protocol demonstrated 19 examples. Pd-catalyzed intramolecular double C–H activation were used key steps in formal total synthesis antimalarial natural product isocryptolepine.

The plethora of transformations attainable by the transition-metal-catalyzed reactions arynes has found immense contemporary interest in scientific community. This review highlights scope and importance aryne field synthetic organic chemistry reported to date. It covers achieved combination various transition metals, which provide a facile access biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, heterocycles, complex natural products. 1 Introduction 2 Insertion...

Abstract Herein, an air‐stable, molecularly defined NNN−Mn(II) pincer complex catalyzed acceptorless dehydrogenative coupling of alcohols with indoles is reported. A wide variety symmetrical and unsymmetrical bis(indolyl)methane derivatives as well some structurally important products such Vibrindole A, Turbomycin B alkaloid, Antileukemic, Anticancer agents were synthesized. Mechanistic studies illustrate the importance NH moiety in crucial role metal‐ligand cooperation during catalysis....

The study describes a novel and general protocol for metal-free intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, sulfur) bond, enabling direct access to the bioactive ampakine quinazolinone class molecules. cross-coupling natural or unnatural amino acid based electrophiles with phenols, amides, thiophenols via organophotoredox catalysis represents an innovative approach towards synthesis heterocycles. present utilizes photochemical single electron oxidation...

The study describes a novel and general protocol for metal-free intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, sulfur) bond, enabling direct access to the bioactive ampakine quinazolinone class molecules. cross-coupling natural or unnatural amino acid based electrophiles with phenols, amides, thiophenols via organophotoredox catalysis represents an innovative approach towards synthesis heterocycles. present utilizes photochemical single electron oxidation...

This study describes a novel and general protocol featuring organophotoredox-catalyzed intramolecular decarboxylative construction of carbon-heteroatom (oxygen, nitrogen, sulfur) bonds, enabling direct access to ampakine APIs (CX-614 CX-554), quinazolinone alkaloids (deoxyvasicinone mackinazolinone), thiazinone scaffolds as well their congeners with broad functional group tolerance scalability. Mechanistic studies suggest radical-polar crossover pathway via single-electron oxidation.

A regioselective quinazolinone-directed ortho lithiation on an adjacent quinoline moiety has been used as a key step for short, efficient, and practical synthesis of the human DNA topoisomerase I poison luotonin luotonins B E. The quinazolinoylquinoline 5 treatment with in situ-generated nonnucleophilic mesityllithium furnished desired dilithiated intermediate 6, which formaldehyde followed by Mitsunobu ring closure reaction gave (1a) very good yield. 6 DMF directly (1b) 81% Luotonin...

Activation of DMSO to work as an economical and environmentally benign one-carbon synthon has been achieved by using a bench-top reagent ammonium persulfate for general efficient access symmetrical methylenebisamides from primary amides.

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTConcise and Efficient Synthesis of Bioactive Natural Products Pegamine, Deoxyvasicinone, (−)-Vasicinone†Santosh B. Mhaske Narshinha P. ArgadeView Author Information Division Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India [email protected]Cite this: J. Org. Chem. 2001, 66, 26, 9038–9040Publication Date (Web):November 22, 2001Publication History Received18 July 2001Published online22 November inissue 1 December...

A facile, fluoride-induced transition-metal-free chemoselective α-arylation of β-dicarbonyl compounds (malonamide esters) at room temperature using aryne intermediates has been demonstrated. Selective mono- or diarylation and generation a quaternary benzylic stereocenter have also achieved. The methodology will be highly useful for the synthesis library CNS depressant barbiturate drugs like Phenobarbital.

An efficient process for the preparation of valuable o-methyl trifluoromethyl sulfide substituted benzophenones has been developed. The transition-metal-free method features insertion aryne into a C-C σ-bond under mild reaction conditions first time to achieve ortho-difunctionalized arenes containing pharmaceutically important trifluoromethylthio functional group. A wide substrate scope demonstrated developed protocol.

The Pd-catalyzed quinazolinone-directed regioselective monoarylation of aromatic rings by C–H bond activation is developed. A broad substrate scope demonstrated for both quinazolinone as well diaryliodonium triflates. use a base was found to be crucial this transformation, unlike the known nitrogen-directed arylations. All novel quinazolinones biological interest were synthesized using operationally simple Pd(II)-catalyzed arylation reaction.

Controlled and efficient activation is the crucial aspect of designing an effective prodrug. Herein we demonstrate a proof concept for light activatable prodrug with desired organelle specificity. Mertansine, benzoansamacrolide, microtubule-targeting compound that binds at or near vinblastine-binding site in mitochondrial region to induce mitotic arrest cell death through apoptosis. Despite its efficacy even nanomolar level, this has failed stage 2 human clinical trials owing lack drug...

Palladium-catalyzed cyclization of imines has been developed to construct the extremely rare 3H-pyrrolo[2,3-c]quinoline ring system for diversity oriented first total synthesis antimalarial marine natural product Aplidiopsamine A as well Marinoquinoline and potential hybrid NCLite-M1.

An unusual nucleophilic nitration of arynes by NaNO2 in the presence water has been developed, and concept was further demonstrated to accomplish a double functionalization using multicomponent reaction protocol synthesize pharmaceutically important (2-nitrophenyl)methanol derivatives. Such substitution ortho −NO2 is difficult other means. The conditions are mild avoid use strong acids, expensive transition metal catalysts, additives.

A Pd(II)-catalyzed intramolecular tandem olefin amidation/C–H activation protocol has been developed for the synthesis of an 8-oxoprotoberberine core. It was successfully applied syntheses (±)-8-oxocanadine, (±)-8-oxotetrahydropalmitine, and (±)-8-oxostylopine, which can be easily converted to respective protoberberine natural products. The short synthetic route demonstrated would useful a large number products their analogues featuring scaffold.

Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines anhydrides. A plausible radical mechanism involving DMSO proposed. The application this facile imide forming demonstrated practical vernakalant.

A novel reactivity of sulfur ylides has been demonstrated in a transition-metal-free protocol to access ortho-substituted thioanisole derivatives by insertion arynes into C–S σ-bond moderate good yields. The reaction involves the formation C–C and bonds consecutive breaking two under operationally mild conditions.

Ru-catalyzed regioselective cascade annulation of acrylamides with 2-alkynoates via aza-Michael/C-H activation sequence for the synthesis various 6-oxo nicotinic acid esters is described. The regioselectivity protocol has been confirmed by performing silver mediated protodecarboxylation corresponding to furnish 2-pyridone. developed copper or salt-free and uses inexpensive, safe, environmentally benign peroxide-based "oxone" as sole oxidant. A redox-neutral version also demonstrated.