O-(2-Aminobenoyl)-Hydroxylamine—A New Reagent for the Direct Conversion of Audehydes to Nitriles

Refluxing an ethanolic solution of O-(2-aminobenzoyl) -hydroxylamine (1) aldenydes and BF₃-Et₂ yields (78–94%) the corresponding nitriles.     

Solvent-Free Conversion of N,N-Dimethylhydrazones to Nitriles Under Microwave Irradiation

A variety of aldehyde N,N-dimethylhydrazones are rapidly converted into the corresponding nitriles using oxone supported on wet Al₂O₃ under microwave irradiation in dry media.     

Jasmonoids: Part 1. Dicarbanion Alkylation Approach to Synthesis of Z-Jasmone/Dihydrojasmone

Application of the dicarbanion alkylation strategy to 2-acetyl-4-methyl-butyrolactone 1 has resulted in a 4 step/5 step synthesis of dihydro-jasmone 6a/z-jasmone 7 respectively.     

Highly Efficient and Selective Deprotection Method for Prenyl,Geranyl, and Phytyl Ethers and Esters Using Borontrifluoride–Etherate

An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride–etherate (BF₃ · OEt₂) at room temperature in good to excellent yields for the first time.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

New and Practical Synthesis of Montelukast Sodium,an Antiasthmatic Drug

Abstract

A new and practical synthesis of montelukast sodium, an antiasthmatic drug, is described. The key steps are the synthesis of nitrile derivative 4 by chiral reduction of keto ester 9 using (?)-DIP-Cl, synthesis of vinylquinoline framework 16 by Wittig reaction, and Heck coupling of nitrile 4 with vinylquinoline 16. The method is operationally simple and suitable for the industrial production of the drug substance.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

Synthesis of Novel Fluorinated 11H‐Azaindolo[3,2‐c]isoquinolines

A series of novel fluorinated 11H‐azaindolo[3,2‐c]isoquinolines ( 7 ) have been synthesized starting from 2(1H)pyridones ( 1 ) via azaindoles ( 5 ). Initially, compound 1 was treated with POCl₃/DMF, and the resulting compound 2 was reacted with benzylamine to obtain compounds 3 that were subjected to cyclization after protecting the secondary amine to get azaindoles ( 5 ). Further, compounds 5 were subjected to cyclization as per Pictet–Spengler reaction condition. However, it was not successful. Subsequently, the azaindoles ( 5 ) were acetylated and then cyclized to give title compounds 7 . These compounds are new and well characterized by spectral data.     

A Novel and Convenient Synthesis of E,E-bis(Styryl) sulfones and E,E-1,4-Diaryl-1,3-butadienes

The condensation of 2-phenylethanesulfonylacetic acid (4) with araldehydes (5) in presence of a base gave E-styryl-2-phenylethyl sulfones (6) which on dehydrogenation with DDQ (7) yielded E,E-bis-(styrl)sulfones (8). The 8 on treatment with dichlorotris(triphenyl-phosphine)ruthenium(II) catalyst resulted 1,4-diaryl-1,3-butadienes (9). The configurations of 6, 8 and 9 have been determined based on IR and ¹H NMR spectral data.     

Zinc-Mediated Facile and Efficient Chemoselective S-Alkylation of 5-Aryl-1,3,4-oxadiazole-2-thiols in the Absence of Base

Zinc-mediated facile and efficient chemoselective S-alkylation of 5-aryl 1,3,4-oxadiazole-2-thiols in the presence of a catalytic amount of tetra butyl ammonium iodide was described. The reaction was performed under neutral conditions. The chemoselectivity of the alkylation was confirmed by NMR spectroscopy and x-ray crystallography.     

Oxone as a Mild,Inexpensive, and Environmentally Benign Oxidant for the α-Thiocyanation of Ketones

An efficient and direct approach for the α-thiocyanation of ketones with α-hydrogens has been developed using ammonium thiocyanate as a thiocyanating agent and oxone as an oxidant in methanol.     

Sonochemical Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles in Aqueous Medium

An ultrasound‐accelerated fast and efficient three‐component reaction for the regioselective synthesis of l,4‐disubstituted 1,2,3‐triazoles using different alkyl and allyl halides, terminal alkynes, and sodium azide in water at room temperature has been developed using CuI as catalyst. Ultrasonication dramatically decreases the reaction times.