2.4- Dimethyl phenyl acetic acid

The reaction of potassium 3-amino-4-oxo-3,4-dihydroquinazoline-2-thiolate 62 with a-bromophenylacetic acid 63 resulted in the formation of (3-amino-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)-phenyl-acetic acid methyl ester 64 which on alkali treatment and subsequent acidification resulted in the synthesis of 2-phenyl- 1-thia-4,4a,9-triaza-anthracene-3,10-dione 65 <1999JCR(S)86>. Similarly, the reaction of potassium 3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- pyrimidine-2-thiolate 66 with a-bromo-ester 67 resulted in the formation of 2-(3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- / pyrimidin-2-ylsulfanyl)-propionic acid ethyl ester 68. Subsequent treatment with alkali followed by acidification resulted in the formation of 2,3,7-trimethyl-3a,9a-dihydro-l,8-dithia-4a,5,9-triazacyclopenta[ ]naphthalene-4,6-dione 69 <2000JHC1161>... 

On further oxidation to the final product all the carbon groups of the side chain are completely oxidized and the products are as above, the dimethyl benzenes and toluic acids yielding di-carhoxyl ring acids while ethyl benzene and phenyl acetic acid yield the mono-carboxyl ring acid. This realtionship shows clearly the difference in character between a ring carboxyl acid and an isomeric side-chain carboxyl acid. Because of its isomerism with toluic acid phenyl acetic acid is also known as alpha-toluic acid, a name that does not seem advisable. While phenyl acetic acid is not of especial importance, the other side-chain carboxyl acids which we shall mention are of considerable importance. 

H-Indole, 3,3-dichloro-synthesis, 4, 369 3H-Indole, 3,3-dimethyl-synthesis, 4, 224 3H-Indole, 3-hydroperoxy-autoxidation, 4, 247 rearrangement, 4, 249 3H-Indole, 3-oximino-synthesis, 4, 209, 210 3H-Indole, 3-oximino-2-phenyl Beckmann rearrangement, 4, 210 Indoleacetic acid synthesis, 4, 337 Indole-3-acetic acid as growth regulator, 4, 372 synthesis, 4, 346 Indole alkaloids, 4, 373 synthesis, 4, 276... 

In asymmetric Strecker synthesis ( + )-(45,55 )-5-amino-2,2-dimethyl-4-phenyl-l,3-dioxane has been introduced as an alternative chiral auxiliary47. The compound is readily accessible from (lS,25)-2-amino-l-phcnyl-l,3-propancdioI, an intermediate in the industrial production of chloramphenicol, by acctalization with acetone. This chiral amine reacts smoothly with methyl ketones of the arylalkyl47 or alkyl series48 and sodium cyanide, after addition of acetic acid, to afford a-methyl-a-amino nitriles in high yield and in diastereomerically pure form. 

A solution of 20.7 g (0.1 mmol) of (46 ,56 )-5-amino-2.2-dimethyl-4-phenyl-l,3-dioxane and 19.4 g (0.1 mol) of 3,4-dimethoxyphenyl-2-propanone in 70 mL of CH3OH is warmed to 60 "C and 9 mL of acetic acid is added. After 15 min the mixture is cooled with an ice bath. The precipitated product is filtered off, stirred with 1 L of water for 1 h to dissolve inorganic salts, and again collected by filtration. Drying over NaOH and recrystallization from CH3OH gives the product yield 33.6 g (82%) mp 127 128°C [a] 2 + 85.7 (c = 1, CHC1,). 

The nitration of dimethyl (Af-phenyl-Ar-methylamino)methylthiomethy-lenemalonate with nitric acid in acetic acid at room temperature for 24 hr gave the 4-nitro derivative (1577) in 38% yield (69T4649). 

Polymers containing pendant carbamate functional groups can be prepared by the reaction of phenyl isocyanate with poly(vinyl alcohol) in homogeneous dimethylsulfoxide solutions using a tri-ethylamine catalyst. These modified polymers are soluble in dimethyl sulfoxide, dimethylacetamide, dimethylformamide and formic acid but are insoluble in water, methanol and xylene. Above about 50% degree of substitution, the polymers are also soluble in acetic acid and butyrolactone. The modified polymers contain aromatic, C = 0, NH and CN bands in the infrared and show a diminished OH absorption. Similar results were noted in the NMR spectroscopy. These modified polymers show a lower specific and intrinsic viscosity in DMSO solutions than does the unmodified poly(vinyl alcohol) and this viscosity decreases as the degree of substitution increases. 

ML-3000 ((2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)-acetic acid) is a nonantioxidant dual inhibitor of both cyclooxygenase and 5-lipoxygenase. ML-3000 has been compared to indomethacin in a number of experimental models of inflammation. The analgesic effects of ML-3000 have also been assessed in a number of animal models. Phase II studies have shown a wide range of activities, including anti-inflammatory, analgesic, antiplatelet and antiasthmatic properties (Laufer et al., 1994 Chin and Wallace, 1999). 

Heating of a mixture of 2-phenyl-1,4-naphthoquinone (1 eq.) with dimethyl malonate (4 eq.) and manganese(III) acetate (6 eq.) in acetic acid at 80°C for 16 hours gives 1 in 76% yield, and this has been shown to be a general type of reaction for a variety of 2-aryl-l,4-naphthoquinones. 

Benzoylamino-6 -pyrido[l,2-a]pyrimidin-6-one 224 was prepared starting from 2-methylpyrimidine and N.TV-dimethylformamide dimethyl-acetate in boiling dimethylformamide (91BSB533). Then the resulting 2-[( )-2-(N,N-dimethylamino)ethenyl)]pyrimidine was reacted with 2-phenyl-5(4//)-oxazolone in refluxing acetic acid to give 6-oxopyrido-[l,2-a]pyrimidine 224 in 33% yield. 

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