2-formylphenyl methyl

Formylphenyl Methyl Tellurium1 20 g (0.05 mol) of 2-formylphenyl dimethyl telluronium iodide are dissolved in 100 m/of pyridine and the solution is heated under reflux for 3 h. The solution is then cooled and poured into a mixture of ice and dilute hydrochloric acid. The mixture is extracted with diethyl ether, the extract is washed with water, dried with magnesium sulfate, the solvent is distilled off, and the residue is fractionally distilled under vacuum yield 9.8 g (77%) b.p. 120 13070.1 torr (13.3 Pa). 

Blount and Robinson have extended this mode of synthesis to the preparation of iV-methyl/iomogranatonine (XXII) by the use of adipaldehyde, CHO. [CH2]4. CHO. The base, on reduetion with sodium in butyl aleohol, yields A -methyl/mmogranatoline (XXII CO — CHOH), the benzoyl derivative of which possesses marked local anaesthetic aetion. Similarly Blount, by eondensing /3-(o-formylphenyl)propaldehyde, CHO. CgH4. CHj. CHj. CHO, with methylamine and calcium acetonedicarboxylate, has prepared 8 9-benz-d - -feomogranatene-3-one (XXIII), which was reduced to the -alcohol (cf. reduction of tropinone to -tropine) and the latter converted to the benzoyl-derivative (m.p. 98°),... 

Chiacchio and co-workers <97T13855> reported a stereoselective synthesis of 133 via an intramolecular 1,3-dipolar cycloaddition. Intermediate 132 was generated in situ by the reaction of tra .v-/V-(2-formylphenyl)-i -methyl-2-phcnylcthenc- l -sulfonamide 131 with N-methylhydroxylamine and afforded a tricyclic benzothiazine 133 in 51% yield (Scheme 36). 

In 1992, Molina et al. synthesized partial structures of lavendamycin using the aza-Wittig reaction as the main strategy (68) to form a /3-carboline at the 2-position of a quinoline (Scheme 23) (68). The reactions of the iminophosphorane 194, prepared from 3-formyl-l-methyl indole by treatment with ethyl azidoacetate and triphenylphosphine, with the 2-formyl-quinoline derivatives 195 in toluene at 160°C in a sealed tube gave the corresponding quinoline derivatives 196 and 197. Treatment of iminophosphorane 194 with pyruvaldehyde yielded the key j3-carboline intermediate 198, which was reacted alternatively with the 2-aminobenzaldehyde 199 and JV-(0-formylphenyl)triphenyliminophosphorane 200 to obtain the corresponding partial structures of lavendamycin, 201 and 202, respectively. 

Lin JM, Yamada M (1998) Electrogenerated chemiluminescence of methyl-9-(p-formylphenyl) acridinium carboxylate fluorosulfonate and its applications to immunoassay. Microchem J 58(1) 105-116. doi 10.1006/mchj.1997.1539... 

R = H, D) were obtained from the 6-methyl-3-ester derivative and its 6,7,8-deuterio derivative 291 (R = Me, R = COOEt, R -R" = H, D). These derivatives were transformed into 293 (R = H, D) by heating in POCI3. Optically active 291 (R = Me, R = COOEt, R -R = H) afforded optically active 6,7-dihydro-477 294 (R = H), but optically inactive AH-pyrido[l, 2-a]pyrimidine 293 (R = Me, R = COOEt, R = H). Similarly ethyl 9-(A -phenyl-iV-methylamino)-6-methyl-4-oxo-6,7-dihydro-4/7-pyrido[l,2-a] pyrimidine-3-carboxylate gave 9-[iV-(4-formylphenyl)-A -methylamino]-7-dimethylaminomethylene-6-methyl-6,7-dihydro-4-oxo-4/f-pyrido[l,2-u]pyr-imidine-3-carboxylates in a mixture of POCI3 and DMF at lower (20-25 °C) and higher (95 100°C) temperatures, respectively. 9-(Ethoxycarbonyl-methyl)-4-oxo-6,7-dihydro-47/-pyrido[l,2-a]pyrimidine-3-carboxylate 158 (but not 9-ethoxycarbonylmethylene-6,7,8,9-tetrahydro derivative 157) was also transformed into ethyl 9-(ethoxycarbonylmethyl)-7-(l-chloroethyl)-4-oxo-477-pyrido[l, 2-a]pyrimidine-3-carboxylate (99T10221). 

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