Flick E.W.'s Adavanced Cleaning Products Formulations vol.4 PDF

By Flick E.W.

ISBN-10: 0815513968

ISBN-13: 9780815513964

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The initial products obtained can suffer further reaction in the presence of a second nucleophilic group to give cyclization products. For didactic reasons, these reactions have been sorted by the nature of the nucleophile. 1 - Amines and related compounds a) Ammonia, hydroxylamine and hydrazine Isatin reacts with ammonium hydroxide or ammonium acetate to furnish a mixture of compounds. Amongst them are isamic acid and its corresponding amide, isamide. Since 1877 there had been a discussion as to their structure, which in 1976 was finally elucidated, by Sir John Cornforth on the basis of chemical and spectroscopic data228.

The same conversion can be realized by ozonolysis161, acidic bromate162 or by a chemiluminescent autoxidation of indigo163. NMethylisatin is also obtained in the photooxidation of N-methylindole-3-acetic acid164. Isoindigo, obtained from isatin and oxindole, is converted diastereoselectively into diazacrisenodiones by reduction with Zn/AcOH, and subsequent acid-catalyzed rearrangement148 (Scheme 37). com/orgchem/0010004 Uploaded 17 October 2000 at 14:44 GMT Please use CPS: orgchem/0010004 in any reference to this article 33 H N O O O O+ N H N H AcOH, HCl, ∆ (100%) O N H H N H N O HCl 4N, ∆ (85%) Zn, HCl O N H H O O H N H Scheme 37 Isatin oximes have also been reduced to 3-aminooxindoles by use of SnCl2/HCl165 or by electrochemical means166,167.

Oxindoles can be prepared by the reduction of dioxindoles or isatins: by using red phosphorous and iodic acid134; by reduction of isatin with H2S in a pyridine/co-solvent mixture1137; by reduction of the isatin-3-ethylene thioketal with Raney nickel138 or by the Wolf-Kishner reaction139-142, where the use of lower molecular weight alcohols as solvent, such as EtOH or iPrOH, lead to high yields of the desired product143. It has however been found that isatin could be reduced to the corresponding oxindoles in high yields (76-92%) by the use of hydrazine hydrate as the solvent in the absence of any additional base144,145.

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