An efficient and novel approach for the synthesis of substituted N-aryl lactams

Activation of C−H bonds and their application in cross coupling chemistry has received a wider interest in recent years. The conventional strategy in cross coupling reaction involves the pre‐functionalization step of coupling reactants such as organic halides, pseudo‐halides and organometallic reagents. The C−H activation facilitates a simple and straight forward approach devoid of pre‐functionalization step. This approach also addresses the environmental and economical issues involved in several chemical reactions. In this account, we have reported C−H bond activation of small organic molecules, for example, formamide C−H bond can be activated and coupled with β‐dicarbonyl or 2‐carbonyl substituted phenols under oxidative conditions to yield carbamates using inexpensive copper catalysts. Phenyl carbamates were successfully synthesized in moderate to good yields by cross dehydrogenative coupling (CDC) of phenols with formamides using copper catalysts in presence of a ligand. We have also prepared unsymmetrical urea derivatives by oxidative cross coupling of formamides with amines using copper catalysts. Synthesis of N,N‐dimethyl substituted amides, 5‐substituted‐γ‐lactams and α‐acyloxy ethers was carried out from carboxylic acids using recyclable CuO nanoparticles. Copper nanoparticles afforded N‐aryl‐γ‐amino‐γ‐lactams by oxidative coupling of aromatic amines with 2‐pyrrolidinone. Reusable transition metal HT‐derived oxide catalyst was used for the synthesis of N,N‐dimethyl substituted amides by the oxidative cross‐coupling of carboxylic acids and substituted benzaldehydes. Overview of our work in this area is summarized.

show abstract

“…Organic carbamates are important building blocks in agrochemicals and pharmaceuticals (Scheme ) and also used as protecting groups …”

Section: Coupling Chemistrymentioning

confidence: 99%

Copper Catalyzed C−H Activation

Kantam

Gadipelly

Deshmukh

et al. 2018

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…207 The IrCl 3 -catalysed IO 4 − oxidation of ethylamine in HClO 4 was first order in Ir(III), fractional order in ethylamine, and zero order in oxidant; the rate increased with [H + ]. 208 The Ru(III)-catalysed oxidation of erythritol (Ery) and dulcitol (Dul) in HClO 4 was of zero order in IO 4 − , less than unit order in Ru(III), and first order in Ery and Dul at low concentrations but approaching zero order at higher concentrations; H + ions catalysed the rate, and Ru(VIII) was believed to be the effective catalytic species. 209 The Rh(III)-catalysed acidic IO 3 − oxidation of 1,2-propanediol to acetic and formic acid was zero order in diol and of inverse fractional order in H + and Cl − ions.…”

Section: Halogensmentioning

confidence: 99%

“…The proposed mechanism 353 is almost similar to the mechanism (Scheme 9) discussed for the homogeneous hydrogenation of ketones, catalysed by complex (203), 354 which suggested the formation of a reactive intermediate dearomatized species (204), which was stabilized by reversible addition of EtOH to form the complex (205). Next (204) coordinated with the ketone and isomerized to intermediate (206), which facilitated the insertion of the ketone into the Fe−H bond giving the pentacoordinated complex (207) which on reaction with H 2 gave the aromatic hydrido alkoxy complex (208). The species (204) was regenerated on the elimination of the product alcohol (Scheme 22).…”

Section: Me Mementioning

confidence: 99%

Oxidation and Reduction

Mehrotra

2014

Organic Reaction Mechanisms Series

View full text Add to dashboard Cite

“…On the other hand, carbamates are a family of organic compounds with multiple applications in the textile industry, agriculture and especially in the design of new enzyme inhibitors and drugs, making attractive the development of novel compounds with this structural motif, [15] which is usually accessible only by the employment of harmful reagents such as phosgene or its derivatives. [16] …”

Section: Introductionmentioning

confidence: 97%

Synthesis of Optically Active Heterocyclic Compounds by Preparation of 1,3‐Dinitro Derivatives and Enzymatic Enantioselective Desymmetrization of Prochiral Diamines

Ríos‐Lombardía¹,

Busto²,

Gotor‐Fernández³

et al. 2010

Eur J Org Chem

View full text Add to dashboard Cite

A general approach for the highly efficient chemical preparation of novel optically active 2‐substituted propane‐1,3‐diamines is described. Diamines have been obtained from the corresponding commercially available aldehydes in a straightforward two‐step synthesis via the corresponding 1,3‐dinitro compounds, which were hydrogenated under mild reaction conditions by using platinum dioxide as the catalyst. Subsequent enzymatic enantioselective desymmetrization mediated by Pseudomonas cepacia lipase allowed the recovery of a family of monocarbamates in good to high enantiomeric excesses (70–90 % ee).

show abstract

An efficient and novel approach for the synthesis of substituted N-aryl lactams

Cited by 21 publications

References 33 publications

Copper Catalyzed C−H Activation

Copper Catalyzed C−H Activation

Oxidation and Reduction

Synthesis of Optically Active Heterocyclic Compounds by Preparation of 1,3‐Dinitro Derivatives and Enzymatic Enantioselective Desymmetrization of Prochiral Diamines

Contact Info

Product

Resources

About