Succinimide 2-phenyl

Fig. 2-11. The effect of flow rate on the selectivity of a-methyl-a-phenyl succinimide on teicoplanin CSP (250 X 4.6 mm) in normal phase. The mobile phase was ethanol hexane (20/80 v/v) at ambient temperature (23 °C).

Ethosuximide is the last antiseizure drug to be marketed whose origin is in the cyclic ureide structure. The three antiseizure succinimides marketed in the USA are ethosuximide, phensuximide, and methsuximide. Methsuximide and phensuximide have phenyl substituents, whereas ethosuximide is 2-ethyl-2-methylsuccinimide. 

In 1996, a group from Sandoz (now part of Novartis) reported their synthesis of fexofenadine (3). Cbz protection of commercially available ethyl piperidine-4-carboxylate (34) was achieved using Af-(benzyloxycarbonyloxy)succinimide to afford 35. Treatment of 35 with three equivalents phenyl magnesium bromide led to tertiary alcohol... 

Bromination of cinnamic acid with NBS in aq. MeOH gives 2-bromo-3-methoxy-3-phenyl propionic acid, PhCH(0Me)CHBrC02H. At moderately high [H+] the reaction is second-order and independent of [H+], whereas at low [H+] the rate increases with decrease in [H+], Succinimide inhibits the reaction182. 

We have developed a new photoreactive analogue of paclitaxel, 3 -N-BzDC-3 -N-debenzoylpaclitaxel (109) and its ditritiated derivative ([3H]-109) has been evaluated for its ability to photolabel tubulin and P-glycoprotein.66 Radiolabeled photoreactive analogue [3H]-109 was synthesized by N-acylation of 3 -N-deben-zoyl-2, 7-bis(0-TES)paclitaxel (108) with N-(2,3-ditritio-3-(4-benzoyl-phenyl)propanoyloxy)succinimide ([3H]-107), followed by purification on a reversed phase semipreparative HPLC using a C-18 column (Scheme 21).66 Photoaffinity label [3H]-109 was assessed to possess >99.9% radiochemical purity and a high specific radioactivity (34 Ci/mmol). 

Some reductases isolated from tobacco (Nicotiana tabacum) were found to exhibit excellent enantioselectivities on the reduction of a number of a,/i-unsaturated compounds [140,141]. For example, reductase p44 catalyzed the asymmetric reduction of A-phenyl-2-methylmaleimide. yielding the enantiopure (7 )-succinimide. Reductase p90 mediated the enantioselective hydrogenation of a number of methyl or ethyl substituted cyclopentenones and cyclohexanones (Fig. 20). 

Enantiomer separation of various compounds such as barbituric acids, benzoin, MTH-proline, glutethimide, a-methyl-oc-phenyl-succinimide, y-phenyl-y-butyrolac-tone, methyl-mandelate, l-(2-naphthyl)ethanol, mecoprop methyl, diclofop methyl and fenoxaprop methyl by pressure supported CEC on a permethyl-P-cyclodextrin modified stationary phase was described by Wistuba and Schurig [42-44]. Three different separation beds were used (i) permethyl-P-cyclodextrin was covalently attached via a thioether to silica (Chira-Dex-silica) [42], permethyl-P-cyclodextrin was linked to a dimethylpolysiloxane and thermally immobilized (ii) on silica (Chirasil-Dex-silica) [43] or (iii) on a silica monolith (Chirasil-Dex-monolith) [44], respectively. 

Another method of hydroxyselenenation involves trapping the seleniranium ion by water. The use of N-phenyl eleno-succinimide (N-PSS) or -phthalimide (N-PSP) as the selenium electrophile facilitates the reaction, since the sucdnimide or phthalimide anion is not as nucleophilic as water. With dienes, trans-annular cyclizations can occur, forming bis(phenylseleno) ethers in good yields (equation 22). ... 

Azulen 3-Acetyl-2-amino-l-aminocarbonyl- V/2c, 230 3,7-Diaza-bicyclo 3.3.0]oct-2-en 6,8-Dioxo-7-methyl-2-phenyl-EI4b, 84 [R —C( = N —R) — NH-CH2-SiR3 + R-X/ Succinimid]... 

Preparation of the dihydrotriazole from ( )-crotonate and phenyl azide, which was unsuccessful under normal conditions74, was achieved under high pressure, although the a-amino diazo compound was the prevalent product78. IV-Aryl succinimides were suitable substrates for... 

Additions of the Michael type of nucleophiles to the carbon-carbon double bond of thiete 1,1-dioxides to give 3-substituted thietane 1,1-dioxides occur readily. The addition of hydrogen has been discussed in Section A. Nucleophiles include cyanide, the anion of nitroethane, the lithium salt of r-butyl o-tolyl sulfone, dimethylamine, cyclohexylamine, ethoxide, and hydrogen sulfide. The reaction is exemplified by the synthesis of 278. Additions to 3-chloro-2H-thiete 1,1-dioxide most likely proceed by an addition-elimination mechanism an example is shown for the addition of the anion of dimethylmalonate to give 279. The replacement of a 3-morpholinyl group by a 3-A methyl-A-phenylamino group in thiete 1,1-dioxide is another example of addition-elimination. An addition of ethoxide with elimination of p-nitrophenyl anion may occur with 268 (Ar = / -N02C6H4). " Addition of bromine via N-bromo-succinimide to the double bond of 4-phenyl-2H-thiete 1,1-dioxide occurs only in 1.5% yield. ... 

The reactivity of the maleimide monomer was dependent on the substitution pattern of the phenyl ring, with the substituents in the ortho position tending to lower the molecular weight of the polymer formed. The THP substituent is readily removed either chemically or thermally to yield poly(iV-(hydroxyphenyl)maleimides). All polymers exhibited excellent thermal stability and showed no evidence of degradation below 360 °C. Reaction occurs between the phenolic ring of the polyimide and HMTA, to form benzoxazine-type derivatives. These reactions have been studied comprehensively using the monomeric model systems, Ai-(hydroxyphenyl)succinimides (Figure 8) . 

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