Current progress in asymmetric Biginelli reaction: an update

The Biginelli reaction, involving a three-component reaction of an aromatic aldehyde, urea and ethyl acetoacetate, has emerged as an extremely useful synthetic tool to organic chemists for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones and related heterocyclic compounds. In the past decades, the asymmetric variants of this reaction have been at the forefront of investigations in several research groups. In 2013, we highlighted the developments occurred in the asymmetric version of the Biginelli reaction. This review article focuses on the recent developments of asymmetric Biginelli reaction covers the literature going back to 2012.     

KHSO_4 as an Efficient Catalytic System for the Regiospecific Nitra-tion of Phenols with Metal Nitrates

Highly regiospecific mononitration of phenol and substituted phenols was accomplished employing a metal nitrate and a catalytic amount of KHSO₄ in acetonitrile. An exclusive ortho‐selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o‐nitrophenols exclusively in good to excellent yields. The use of KHSO₄ is key for the selectivity observed.     

Arylidene pyruvic acids (APAs) in the synthesis of organic compounds

1. Download : Download full-size image

     

Applications of Danishefsky’s dienes in asymmetric Oxo-Diels-Alder reactions

Applications of Danishefsky’s dienes in catalytic asymmetric hetero-Diels-Alder (AHDA) reactions or specifically, their asymmetric Oxo-Diels-Alder (AOxo-DA) reactions with appropriate dienophiles are highlighted in detail, including the preparation of catalysts with discussion from a mechanistic points of view. Danishefsky’s dienes are effective and useful compounds for the synthesis of optically active six-membered rings such as dihydropyrones, dihydropyridones and dihydropyrans. Due to the broad range of the overall subject, we have limited ourselves, to the recent developments in the utility of Danishefsky’s dienes in the reaction with carbonyl compounds (aldehydes, ketones and 1,2-dicarbonyl compounds) in asymmetric Oxo-Diels-Alder (AOxo-DA) reactions.     

Mild,Efficient, and Rapid Dehydration of Aldoximes to Nitriles Mediated by Phthalic Anhydride Under Microwave Irradiation

Summary.  Aldoximes can be efficiently and rapidly dehydrated to nitriles by treatment with phthalic anhydride under microwave irradiation. Received April 18, 2001. Accepted (revised) June 7, 2001     

A Straightforward Method for the Synthesis of Functionalized Trisubstituted Alkenes through Na2S/Al2O3 Catalyzed Knoevenagel Condensation

Na₂S/Al₂O₃ catalyzed the Knoevenagel condensation between an aldehyde and an active methylene compound to yield various trisubstituted alkenes.     

Reductive Dehalogenation of Arylhalides and Alkylhalides with Zinc in THF Saturated Aqueous Ammonium Chloride

A low‐cost and highly effective zinc/THF‐saturated aqueous ammonium chloride has been developed for dehalogenation of arylhalides and alkylhalides in aqueous systems.     

A novel three-component reaction for the synthesis of 3-aryl-4H-benzo [1,4] oxazin-2-amine

A high yielding and fast method for the synthesis of 3-aryl-4H-benzo [1,4] oxazin-2-amine via one-pot, three component reaction of an aromatic aldehyde, isocyanide and o-aminophenol using p-toluene sulfonic acid as a catalyst is described.     

Organic synthesis in water: a green protocol for the synthesis of 2-(cyclohexylamino)-3- aryl- indeno[1,2-b]furan-4-ones

Aldehydes, 1,3-indandione and cyclohexylisocyanide undergo smooth coupling-cyclization in water to produce the corresponding 2-(cyclohexylamino)-3-aryl- indeno [1,2-b] furan-4-ones in good yields. Water was used as a solvent to avoid the use of other highly toxic and environmentally unfavorable solvents for this synthesis.

---

Graphical Abstract  A simple and efficient synthesis of 2-(cyclohexylamino)-3-aryl- indeno[1,2-b]furan-4-ones was achieved via a one-pot three-component reaction of cyclohexylisocyanide, aldehydes, and 1,3-indandione in water for 5 h in good yields. zFX