A new, mild and high yielding protocol for the preparation of nitriles from aldehydes using iodosobenzene diacetate in aqueous ammonia
Seema Bag, Nilesh R. Tawari, and Mariam S. Degani*
Institute of Chemical Technology, University under Section 3 of the UGC Act 1956, Nathalal Parikh Marg, Matunga, Mumbai-400019, India
E-mail: ms.degani@ictmumbai.edu.in.
Abstract
A new, mild and high yielding protocol was developed for the transformation of aldehydes into nitriles using iodosobenzene diacetate (IBD) in aqueous ammonia under mild reaction conditions at room temperature.
Keywords: Aldehyde, nitrile, iodosobenzene diacetate
Introduction
Transformation of aldehydes into nitriles is of prime importance because of the versatility of nitriles as starting materials for the synthesis of various bioactive molecules of pharmaceutical interest. These are also used for the synthesis of nitrogen-containing functional moieties like triazines, thiazoles, 2-oxazolines, tetrazoles, imidazoles, triazoles which possess a broad spectrum of biological activities. Moreover, the nitriles can be converted to various functional groups such as amides, carboxylic acids, amines, ketones, and esters.1-3
During the course of our research related to the synthesis of novel triazine analogs as anti- infective agents, we were required to synthesize nitriles from their corresponding aldehydes. Therefore, we re-examined various methods reported in literature for the preparation of nitriles from aldehydes. Principally, nitrile can be obtained either by dehydration of aldoximes or by oxidation of aldimines prepared from the corresponding aldehydes under various conditions. Also reagents4-8 such as trimethylsilyl azide,9 triazidochlorosilane,10 sodium azide and aluminium chloride11 can be used. However, the above mentioned methods suffer from various drawbacks such as long reaction times, low yields, drastic reaction conditions, use of hazardous, expensive and easily inaccessible reagents and some of them also involve tedious workup procedures.12
Also, several methods are reported using various reagents in combination with ammonia e.g NH3, H2O2;13 NH3/I2 in THF-water;14-16 NH3/NBS in water.17
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