Synthesis of functionalized isoindoles by the rhodium-catalyzed reaction of cyanoformates with ortho-Borylbenzalacetone derivatives

Bulletin of the Korean Chemical Society

Volumn 31, Issue 6, 2010, Pages 1461-1462

  Shimizu, Hiroshi ^a   Igarashi, Tomohiro ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Azaheterocycles; Cyanoformates; Isoindoles; Ortho Borylbenzalacetone; Rhodium

Indexed keywords

EID: 77953933798     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.6.1461     Document Type: Article

References (19)

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7. A representative procedure for the synthesis of 3-acylmethyl- 2H-isoindole derivatives 3: To a mixture of 1a (78.3 mg, 0.30 mmol), B(OH)3 (55.6 mg, 0.90 mmol), and [Rh(OH)(cod)]2 (3.5 mg, 7.7 (μmol) under an argon atmosphere was added a solution of 2a (90.1 mg, 0.90 mmol) in NMP (0.3 mL). After the reaction mixture was stirred at room temperature for 30 min and then at 80 °C for 3 h, it was cooled and diluted with a mixed solvent of AcOEt and toluene (2 : 1, 5 mL) and H2O (2 mL). The organic layer was separated and the aqueous layer was extracted with the mixed organic solvent (5 mL × 4). The combined extracts were more diluted with the mixed solvent (25 mL), washed with water (10 mL × 3) and with brine, and dried over Na2SO4. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (CHCl3/AcOEt = 5/1) to afford 3a (56.1 mg, 75%).
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