Lidia De Luca

One-Pot Synthesis of Amides from Aldehydes and Amines via C–H Bond Activation

A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed. Both aliphatic and aromatic aldehydes and many types of mono- and disubstituted amines are tolerant in this transformation. This cross-coupling reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.

Some Recent Approaches to the Synthesis of 2-Substituted Benzofurans

In their structural multiplicity and in the extent to which they occur in nature the derivatives of benzofuran are significantly lesser than the isoelectronic analogue indoles. However, these heterocyclic compounds show a variety of pharmacological properties, and change of their structure offers a high degree of diversity that has proven useful for the search of new therapeutic agents. The broad spectrum of pharmacological activity in individual benzofurans indicates that this series of compounds is of an undoubted interest. From this point of view, synthetic methods may be of very useful aid in the production of specific structures characterized by given pharmacological qualities. Moreover from a drug discovery perspective, synthesis of chiral functionalized substituted benzofurans could be more interesting because they might constitute starting materials for the production of biologically active compounds. Taking into account the actual tendency directed toward the development of enantiomerically pure drugs, indeed there is a limited number of papers related to the preparation of enantiomers of benzofuran containing compounds, likely because of difficulties in their preparation with conventional methods. In this context, new approaches seem to expand the potentiality of the synthesis of substituted benzofurans, providing also convenient routes to enantiopure 2-substituted benzofurans.

Iron-catalysed oxidative amidation of alcohols with amines

A new iron-catalysed oxidative amidation of differently substituted benzylic alcohols with mono- and di-substituted amines was developed.

From alcohols to indoles: a tandem Ru catalyzed hydrogen-transfer Fischer indole synthesis.

In a new version of the Fischer indole synthesis, primary and secondary alcohols have been catalytically oxidized in the presence of phenylhydrazines and protic or Lewis acids to give the corresponding indoles. The overall reaction can be accomplished in one step, and the use of alcohols instead of aldehyes or ketones as starting materials has several advantages in terms of a large selection of reagents, easy handling, and safety of the process.

AN EASY MICROWAVE ASSISTED SYNTHESIS OF SULFONAMIDES DIRECTLY FROM SULFONIC ACIDS

An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.

A method for generating nitrile oxides from nitroalkanes: a microwave assisted route for isoxazoles

A convenient route has been developed for generation of nitrile oxides in situ from nitroalkanes under very mild conditions using microwave irradiation, using 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) and DMAP as catalyst. Isoxazolines and isoxazoles are obtained in very good yields compared to known methods.

Microwave-Promoted Selective Mono-N-Alkylation of Anilines with Tertiary Amines by Heterogeneous Catalysis

A palladium-catalyzed N-alkylation of anilines with tertiary amines that occurs under heterogeneous transfer-hydrogenation conditions has been developed. This protocol of transamination, which uses a relatively cheap and easily recyclable heterogeneous catalyst, can be efficiently applied to different substrates and is suitable for large-scale preparations.

Synthesis of Substituted Benzofurans via Microwave-Enhanced Catch and Release Strategy

A microwave-enhanced procedure for the synthesis of substituted benzofurans starting from 2-(1-hydroxyalkyl)-phenols and using triphenylphosphine polystirene resin is reported. The benzofurans are isolated in good to high yields and purities by simple workup. The procedure can be applied to chiral alpha-alkyl-2-benzofuranmethanamines too.

Synthesis of α , β -unsaturated aldehydes based on a one-pot phase-switch dehydrogenative cross-coupling of primary alcohols

An efficient one-pot ruthenium-catalyzed hydrogen-transfer strategy for a direct access to α,β-unsaturated aldehydes has been developed. The employment of enolates prepared in situ from alcohols avoided handling unstable aldehydes and provided a very appealing route to different cinnamaldehydes substituted in position 2. A silica-grafted amine was used as phase-switch tag leading to a selective one-pot process in favor of cross-dehydrogenative coupling products.

New pyrazole containing bicarboxylic α-amino acids: mimics of the cis amide bond

A series of novel optically active α-amino acids, containing a pyrazole ring, which can be regarded as building blocks for peptidomimetics, have been prepared starting from readily available α-amino acids. The synthetic strategy employed allows the regio- and stereoselective preparation of 1,3- or 1,5-substituted pyrazolyl rings. The pyrazole containing peptidomimetics can be considered as analogues of peptides with a cis amide bond.