Phthalimide derivatives

The synthesis from phthalimide derivatives, eg, diimidophthalamide (or phthalimide [85-41-6]) is usually carried out in a solvent such as formamide. 

Each of the following dihaloalkanes gives an A-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Write the structure of the phthalimide derivative formed in each case and explain the basis for your answer. 

Development of novel response modifiers derived from thalidomide (3-phthaIimidopyridine-2,6-dione) and other phthalimide derivatives 99 YGK94. 

Condensation of o-aminoacetophenone with maleic, succinic or phthalic anhydrides gave 117 whose bromination with CuBr2 gave the bromides 118. Column chromatographic separation of the respective maleimide derivative on silica gel gave the bromoquinoline 119 whereas the phthalimide derivative was obtained from 118 by cyclization with EtsN (93MI11). On the... 

Chloroalkenes are used as 7i-nucleophiIes in the acid-catalyzcd reaction of phthalimide-derived hydroxylactams. These cyclizations lead to sole formation of the thermodynamically less stable e/ r/(t-l-acetylpyrrolo[2,1-(v isoindole derivatives92. 

Note Instead of chlorine gas treatment the chromatograms can be exposed to bromine vapor [8] or sprayed with bleach solution. In the case of phthalimide derivatives the chromatograms are heated for 1 h at 180 °C before chlorine treatment [9]. The colored... 

Figure 4, Highest area sample NMOR levels in a tire factory, showing the reduction achieved. The October 1979 reduction was attributed to venting, the December 1979 reduction to the installation of exhaust canopies, and the February 1980 reduction to use of a phthalimide derivative instead of diphenylnitrosamine...

Systematic studies of the photoreactions of cyclic imides and in particular of phthalimide derivatives have been the subject of a review.278 One of the... 

Kikugawa et al. reported the synthesis of murrayafoline A (7) starting from the A)-(]V,N-diarylamino)phthalimide derivative 630 by reaction with AICI3 in benzene... 

While reaction of the acetate 40 as well as the acetyl- and phthalimide derivatives of chiral amine (41b and 41c) proceeded with erythro diastereoselectivity (in accordance with the classical cis effect, minimization of 1,3-allyhc strain) (Table 6, entries 8, 10, 11), for the allylic alcohols 39, primary allyhc amine 41a, silyl enol ethers 42 and enol ether 43 threo selectivity was observed (Table 6, entries 1-7, 9, 12-14) (see also Scheme 24). For allyhc alcohols with an alkyl group R cis to the substituent carrying the hydroxyl group, diastereoselectivity was high (Table 6, entries 1-7) in contrast, stereoselection was low for allylic alcohols which lack such an R cis) substituent (substrates 39h and 39i, see Figure 4). 

Phthalimide derivative pesticides,liquid, flammable, toxic, n.o.s., flashpoint less than 23 degrees C 2774... 

Phthalimides and Some Tnchloromethylthiocarboximides. The fungicidal efficacy of this chemistry was recognized in the 1950s. The phthalimide derivatives are excellent, broad-spectrum fungicides which can be applied to the foliage roots, or seed of a crop. The most important... 

Polystyrene-bound amines can be converted into the corresponding phthalimides by heating with other phthalimides (BuOH, 85 °C, 18 h [33]). Support-bound phthalimides have also been prepared by N-alkylation of phthalimide derivatives [295] or by amidomethylation of cross-linked polystyrene with /V-(hydroxymethyl) or /V-(chloro-methyl)phthalimide [296,299]. 

When the phthalimide derivative is hydrolysed, primary amines are formed, so that the reaction is useful for preparing certain aliphatic amines. 

N-Vinylsuccinnimide and N-vinylphthalimide were hydroformylated using complex (34) and the ligands DIOP (49), DIPAMP (50) and DIPHOL (85). Optical yields for the resulting 2-imidopropanals of up to 27% for the succinnimide and 38% for the phthalimide derivatives could be obtained, in both cases with (85) as ligand.364... 

About the same time McKervey reported A-sulfonamidoprolinate catalysts [53] (17), and later Ikegami, Hashimoto, and co-workers described uses of dirhodium(II) catalysts with ligands that were phthalimide derivatives of phenylalanine [54] (18a), fer/-leucine [55] (18b), and alanine (18c), but they were similarly unselective in intermolecular cyclopropanation reactions of ethyl diazoacetate. Only when Davies applied chiral prolinate 17a and those that he reported for the first time (17c, X = rBu, C12H25) to cyclopropanation reactions of vinyldiazocarboxylates (Eq. 5.12) did the value of these catalysts for cyclopropanation reactions become fully expressed (Table 5.6) [56,57], The advantage of 17c (X = C12H25) is its solubility in pentane, even at -78°C. 

Acetonide 133 is converted into the phthalimide derivative 135 and further reaction products 136 and 137 via substitution of mesylate 134 with potassium phthalimide (Scheme 44). 

Reaction of rac-1 -tert-buty l-3-chloroazetidin-2-one (28) with 25 gave the rac-phthalimide derivative (29). Optical resolution of rac-29 was accomplished efficiently by complexation with 15. When a solution of 15b and two molar equivalents of rac-29 in benzene-hexane (1 1) was kept at room temperature for 12 h, a crystalline 1 1 inclusion complex of 15b and (-)-29 was obtained. After one recrystallization from benzene-hexane, the crystals were chromatographed on silica gel to give pure complex consisting of (-)-29 of 100% ee in 63% yield. Decomposition of the complex with hydrazine gave optically pine (-)-3-amino- l-/m-butylazetidin-2-onc (30) in 44% yield.15 Mechanism of the precise chiral recognition between 15b and (-)-29 in their 1 1 complex was clarified by X-ray crystal structural analysis.15... 

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