Phthalimido compounds

Phthalimido compounds also photocyclise, e.g. [157] gives [158] (Coyle et al., 1978 Coyle and Newport, 1980 Machida et al., 1977,1980b). Azetidines can be prepared by intramolecular photocyclisation of a-amino methyl ketones (Hesabi et al., 1980). Some Mannich bases have been photocyclised to give a... 

The isocyanates (9) were transformed into amino derivatives by standard reactions. Acid-sensitive aminocyclopropanes were obtained preferentially from benzyr ) -naphthyl or trifluorethyl-urethanes which were cleaved by hydrogen, EtSNa/DMF or alkaline hydrolysis. The hydrazinolysis of phthalimido compounds obtained from the urethane and phthalic anhydride also was useful Trimethylsilylethanol proved to be advantageous for the isocyanate-amine conversion the resulting urethanes gave amines upon addition of Bu4N p- 161 (e.g. synthesis of amine (21) from truns-crysanthemic acid via isocyanate (20) S equation 3). Contrarily to... 

Gabriel reaction. Review.1 The Gabriel reaction is ordinarily not applicable to aryl halides however, under catalysis with cuprous bromide or iodide and in boiling DMA (dimethylacetamide) as solvent, aryl bromides or iodides (but not chlorides) react with potassium phthalimide to give phthalimido compounds in >5-95% yield.2... 

Cleavage of phthaloyl protective group. The phthaloyl group is not useful for protection of the amino group of penicillins and cephalosporins because hydrazinolysis (Ing-Manske procedure, 1, 442) disrupts the azetidinone ring. Eli Lilly chemists have reported a new method of dephthaloylation that overcomes this difficulty. The phthalimido compound (1) is hydrolyzed by aqueous sodium sulfide to the corresponding phthalamic acid (2), which on dehydration... 

Retinylamine and its derivatives can be prepared according to Kienzle (1973) from labeled retinol and phthalimide, diethylazocarboxylate, and triphenyl-phosphine, followed by hydrazinolysis of the intermediate phthalimido compound. 

Exposure of compound 16, a substance that can be obtained in a straightforward manner from glycine, to sodium tert-butoxide furnishes an enolate that undergoes conversion to 8 upon treatment with terf-butyl formate. It was anticipated that the phthalimido and tert-butyl ester protecting groups in 8 could be removed easily and selectively under anhydrous conditions at a later stage in the synthesis. 

Polymers with primary or secondary amine functionality cannot be prepared directly by RAFT polymerization these groups undergo facile reaction with thiocarbonylthio compounds. Such polymers can be prepared indirectly using RAFT agents with latent amine functionality, such as the phthalimido group in... 

Clark et al. [81] determined the time course of A-acetylation of primaquine by Streptomyces roseochromogenous and Streptomyces rimosus by quantitative high performance liquid chromatographic analyses of the culture broths. The A-5-bistri-fluoroacetyl derivative of primaquine was used as an internal standard in the analysis for the quantitation of primaquine A-acetate in microbial culture broths. S. roseochromogenous forms the highest level of primaquine A-acetate at 24—36 h after substrate addition, while S. rimosus is slower in its acetylation, peaking at 3 days after substrate addition. The formation of a novel dimeric compound from the reaction of primaquine with 8-(4-phthalimido-l-methylbutylamino)-6-methoxy quinoline is also reported. 

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

It was also synthesised by E. Fischer in 1901 from 7-phthalimido-propylmalonic ester which he employed in the preparation of ornithine. The bromine derivative of this compound when treated with ammonia gave a complex mixture of products which after hydrolysis by hydrochloric acid at 100° C. gave phthalimide and a-pyrrolidine carboxylic acid —... 

TAT and TAT-HCl are the most available and inexpensive TNT derivatives [39,43, 44]. Catalytic hydrogenation of TNT led to the formation of free TAT [45]. Treatment of this compound with threefold molar amount of phthalic anhydride led to the formation of 2,4,6-tris(N-phthalimido)-toluene (Scheme 4.17), which under the action of hydrazine hydrate was transformed into 2,4-diamino-6-(N-phthalimido)-toluene (Scheme 4.17) [41],... 

Compound was treated with phthalic anhydride in pyridine at 90° for 0.5 hr, then acetic anhydride was added, and the mixture was stirred for another hour at 90° and worked up. The product 39 (34) was isolated as needles in 80% yield, and was then converted into 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-8-D-glucopyranosyl bromide ("glycosyl donor") according to the method reported... 

Among them, the first compound prepared and studied was 3,5-anhydro-1,2-0-isopropylidene-a-D-xylofuranose (87)347 349 and its 1,2-O-cyclohexy-lidene analogue.350 Formation of the oxetane ring is based on the internal substitution of an conventional leaving group X at C-5, or surprisingly, also phthalimido group in 86 351 for application of the Mitsunobu reaction, see Ref. 349. 

Recently, N-hydroxyphthalimide (NHPI) catalysis has been applied to a variety of aerobic oxidations of organic compounds [12], We have reported how NHPI, in the presence of Co(II) salts, is able to generate the phthalimido N-oxyl (PINO) radical, which rapidly abstracts hydrogen from aromatic and aliphatic aldehydes, in a free-radical chain mechanism under aerobic conditions (Scheme 14.2) [13]. The role of oxygen is to oxidize Co(II) to Co(III), which is also involved in the oxidation of the intermediate (Equation 14.8). 

The bleach in a dishwasher tablet or powder is percarbonate and this needs a bleach activator, but now it is possible to add a metal compound as a catalyst because there is no danger of the contents of the dishwasher suffering in the way that some fabrics can be affected. In some tablets a new self-activating bleaching agent, PAP (short for 6-(phthalimido)peroxyhexanoic acid) is used and this needs no activator or catalyst. 

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