SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 17, 2008, Pages 2716-2720

Synthesis of 3-arylideneindolin-2-ones from 2-aminophenols by Ugi four-component reaction and Heck carbocyclization

(3) Dai, Wei Min a,b Shi, Jianyu a Wu, Jinlong a

a ZHEJIANG UNIVERSITY (China)

b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY (Hong Kong)

Author keywords

2 Aminophenol; 2 Oxindole; Aryl triflate; Heck reaction; Ugi four component reaction

Indexed keywords

2 AMINOPHENOL; 3 SUBSTITUTED METHYLENEINDOLIN 2 ONE DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA[N(2 HYDROXYPHENYL)SUBSTITUTED AMIDO]CARBOXAMIDE DERIVATIVE; AMIDE; CINNAMIC ACID; CYANIDE; INDOLE DERIVATIVE; METHANOL; PALLADIUM ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; HECK REACTION; MICROWAVE RADIATION; SYNTHESIS;

EID: 55449125092 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083505 Document Type: Article

Times cited : (36)

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49
- 55449107302
- General Procedure for Synthesis of U-4CR Products 13 A solution of a 2-aminophenol 9 (3.0 mmol) and an aldehyde 10 (3.0 mmol) in MeOH (5 mL) was stirred at r.t. for 15 min. To the resultant mixture was added a carboxylic acid 11 (3.0 mmol) followed by stirring for 5 min. An isocyanide 12 (3.0 mmol) was then added to the above mixture followed by stirring at 50 °C for 48 h. The white precipitate of the U-4CR product 13 was collected by filtration and the solid was washed with MeOH (3 mL, The combined filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography over silica gel [eluting with 20% EtOAc in PE (bp 60-90 °C, to give additional portion of the U-4CR product 13. The yields of U-4CR 13a-g are given in Table 1. Characterization Data for 13d White solid; mp 233-236 °C (CHCl 3-hexane, Rf, 0.26 (20% EtOAc-hexane, IRKBr, 3326, 3030, 1
- 3: C, 78.13; H, 5.92; N, 5.88. Found: C, 78.13; H, 5.91; N, 5.84.

50
- 55449128730
- General Procedure for Formation of Aryl Triflates 14 To a suspension of NaH (1.5 mmol) in dry THF (3 mL) cooled in an ice-water bath was added a solution of the U-4CR product 13 (1.0 mmol) in dry THF (7 mL) under a nitrogen atmosphere. After stirring for 10 min, a solution of PhNTf2 (1.2 mmol) in dry THF (8 mL) was added via a syringe. The resultant mixture was stirred at r.t. for 1 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography over silica gel [eluting with 20% EtOAc in PE (bp 60-90°C, to give the aryl triflate 14. The yields of aryl triflates 14a-g are given in Table 1. Characterization Data for 14d Colorless crystals; mp 146-148°C (EtOAc-hexane, Rf, 0.29 (20% EtOAc-hexane, IR (KBr, 3322, 1681, 1652, 1601, 1366, 1212, 1139cm-1. 1H NMR (400 MHz, CDCl3, δ [major atropisomer 83% in CDCl3 at
- 5S: C, 63.15; H, 4.47; N, 4.60. Found: C, 63.17; H, 4.43; N, 4.51.

51
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52
- 55449090171
- General Procedure for Microwave-Accelerated Synthesis of IMHR Products 15 A 10 mL pressurized process vial was charged with the aryl triflate 14 (0.26 mmol, Pd(OAc)2 (1.3-10-2 mmol, 5 mol, and (±)-BINAP (1.3-10-2 mmol, 5 mol, The vial was sealed with a cap containing a silicon septum. The vial was evacuated and backfilled with N2 (repeated for three times) through the cap using a needle. To the degassed vial was added degassed anhyd MeCN (5 mL) and Et3N (1.04 mmol) through the cap using a syringe. The loaded vial was then placed into the microwave reactor cavity and was heated at 180 0C for 20-60 min. After cooling to r.t. the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography over silica gel [eluting with 17% EtOAc in PE (bp 60-90°C, to give the 3-arylideneindolin-2-ones (E)-15 and (Z)-15. The yields of 15a-g a
- 13C NMR spectra of 15a-g can be found in the Supporting Information.

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