Nitriles aldehydes from

This synthetic process is applicable to the preparation of other aromatic nitriles from aldehydes. The submitters have used it to prepare 5-bromoindole-3-carbonitrile, 7-azaindole-3-carboni-trile, j)-chlorobenzonitrile, 3,4,5-trimethoxybenzonitrile, and p-N,N-dimethylaminobenzonitrile.9 There are several advantages to its use. They include (a) readily available and inexpensive reagents, (b) a simple, time-saving procedure, and (c) fair to good yields of nitrile obtained by a one-step method. 

Efficient One Pot Synthesis of Nitriles from Aldehydes in Solid State Using Peroxymonosulfate on Alumina (Bose and Narsaiah, 1998)... 

Z)-a,f - Unsaturated nitriles. A highly selective synthesis of essentially pure (Z )-a,/ -unsaturated nitriles from aldehydes is possible by use of 1 (equation I).1... 

SECTION 183 Nitriles from Alcohols and Thiol3 No Additional Examples SECTION 184 Nitriles from Aldehydes... 

The adducts derived from aldoximes and carbodiimides are not stable. They undergo dissociation to give nitriles 472. This reaction is a useful synthetic route to produce nitriles from aldehydes and hydroxylamine in the presence of DCC and cupric salts in one step. The reaction of of the oximes with carbodiimides is best conducted in a two phase system (methylenechloride/water) using triethylamine, and the yields are almost quantitative." ... 

A new method, employing 0-(2-aminobenzoyl)hydroxylamine and BF3 Et20, has been discovered for the synthesis of nitriles from aldehydes yields are 78-94 % (Eq. 90) [147]. 

Granacher synthesis via rhodanine Nitriles from aldehydes... 

Nitriles from aldehyde-bisulfite compounds CH(OH)S03H —CH2CN Synthesis with addition of 1 C-atom... 

Homologated nitriles from aldehydes or ketones. This reaction can be carried out in two steps conversion to the 2,4,6-triisopropylbenzenesuIfonylhydrazone (5, 706) followed by reaction of the hydrazone with KCN (equation I). The method is applicable to unsaturated ketones and to substrates containing a hydroxyl group. 

Pyrolysis of pyridine derivatives is a method for allylic and benzylic deamination the preparation of nitriles from aldehydes, and the preparation of isocyanates from acid chlorides or hydrazides Flash vacuum pyrolysis continues to yield interesting reactions and products. Recently, it has been reported that quite sensitive acetylene derivatives can be obtained by this method from 4-alkylideneisoxazol-5(4H)-ones by ring degradation. On the other hand, 2 carbamyl azide molecules cyclize under these conditions to form l,2,4-triazolidine-3,5-dione 1,2-ylids . 2H-Cyclohepta[b]furan-2-ones have been obtained by ring expansion of phenyl propiolates... 

O- (2-Aminobenzoyl)hydroxylaminelboron fluoride Ar. nitriles from aldehydes under mild conditions... 

Reddy, M.B.M. and Pasha, M.A. 2010. Environment friendly protocol for the synthesis of nitriles from aldehydes. Chin. Chem. Lett. 21 1025—1028. 

Sodium hydroxylaminedisulfonate Nitriles from aldehydes via aldoximes... 

An improved method for the preparation of nitriles and thiocyanates from halides with benzyltrimethylammonium salts and a convenient preparation of both aliphatic and aromatic nitriles from aldehydes through N,N,N-trimethylhydrazonium salts have been reported. Nitriles can be easily converted into amidines with ammonium halides . Acylisocyanates can be conveniently prepared from amides with oxalyl chloride . A simple preparation of alkyl and aryl carbamates with N-carbonylsulfamic acid... 

Hajipour, A. R., Ghayeb, Y., and Sheikhan, N. (2010). Zr(HS04)4 catalyzed one-pot Strecker synthesis of a-amino nitriles from aldehydes and ketones under solvent-liee conditions. J. Iran. 

Once again, new reagents for the direct conversion of aldehydes into nitriles have been reported,probably the most useful of which is the modified reductive cyanation procedure which now allows the preparation of nitriles from aldehydes with the addition of one C-atom (Scheme 20). An analogous procedure involves the reaction of potassium cyanide with the 2,4,6-tri-isopropylbenzenesulphonyl (trisyl) hydrazones of both aliphatic aldehydes and ketones (Scheme 21). 

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