Synthesis of 3-alkoxy- and 3-alkylamino-2-alkyl-3-arylisoindolinones

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 997-999

  Kitching, Martin S ^a   Clegg, William ^a   Elsegood, Mark R J ^a   Griffin, Roger J ^a   Golding, Bernard T ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Combinatorial synthesis; Isoindolinones; Regioselectivity; Solvent effect

Indexed keywords

AMINE; ISOINDOLE DERIVATIVE; SOLVENT;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033050411     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3116     Document Type: Article

References (21)

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2. Kubota, Y.; Tatsuno, T. Chem. Pharm. Bull. 1971, 19, 1226. Bhatt, M. V.; El Ashry, S. H.; Somayaji, V. Indian J. Chem. 1980, 19B, 473. Sloan, K. B.; Koch, S. A. M. J. Org. Chem. 1983, 48, 3777. Nishio, T.; Yamamoto, H. J. Heterocycl. Chem. 1995, 32, 883.
3. Kubota, Y.; Tatsuno, T. Chem. Pharm. Bull. 1971, 19, 1226. Bhatt, M. V.; El Ashry, S. H.; Somayaji, V. Indian J. Chem. 1980, 19B, 473. Sloan, K. B.; Koch, S. A. M. J. Org. Chem. 1983, 48, 3777. Nishio, T.; Yamamoto, H. J. Heterocycl. Chem. 1995, 32, 883.
4. Kubota, Y.; Tatsuno, T. Chem. Pharm. Bull. 1971, 19, 1226. Bhatt, M. V.; El Ashry, S. H.; Somayaji, V. Indian J. Chem. 1980, 19B, 473. Sloan, K. B.; Koch, S. A. M. J. Org. Chem. 1983, 48, 3777. Nishio, T.; Yamamoto, H. J. Heterocycl. Chem. 1995, 32, 883.
5. 3-Chloroisobenzofuranone 4 and 3-chloroisoindolinone 6. 2-Benzoylbenzoic Acid (500 mg, 2.21 mmol) or 3-hydroxyisoindolinone 5 (1.59 mmol) was dissolved in dry THF (20 mL). Thionyl chloride (2.21 mmol or 1.59 mmol respectively) and DMF (1 drop) were added. The mixture was stirred overnight. The reaction was monitored by heating a sample of the reaction mixture with dry methanol before TLC analysis. Removal of the solvent in vacuo gave a pale yellow oil 4 (∼ 100%) or 6 (∼ 100%) which was used without further purification.
6. Sloan, K. B.; Koch, S. A. M. J. Org. Chem. 1983, 48, 635.
7. 17, 18
8. All yields in this paper, with the exception of 4 and 6a/b, are for isolated, analytically pure racemates.
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