SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 13, 2009, Pages 2083-2088

Synthesis of heterocycle-annulated medium-sized oxacycles and lactone derivative by intramoleculer heck reaction

(4) Majumdar, K C a Narayan De, Rajendra a Chattopadhyay, Buddhadeb a Roy, B a

a UNIVERSITY OF KALYANI (India)

Author keywords

8 exo trig; Eight membered oxacycle; Intramoleculer heck reaction; Lactone; Palladium acetate

Indexed keywords

HETEROCYCLIC COMPOUND; LACTONE DERIVATIVE; PALLADIUM;

ALLYLATION; ANNULATION REACTION; ARTICLE; CATALYST; CYCLIZATION; HECK REACTION; REACTION TIME; SYNTHESIS;

EID: 68949164931 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217702 Document Type: Article

Times cited : (4)

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- General Procedure for the Synthesis of the Compound by Heck Reaction A mixture of 3a (70 mg, 0.182 mmol, TBAB (147 mg, 0.455 mmol, and dry KOAc (26 mg, 0.265 mmol) was taken in dry DMF (10 mL, Pd(OAc)2 (10 mol, 4.1 mg) was added, and the mixture was stirred on an oil bath at 110°C for ca. 2 h. The reaction mixture was cooled, DMF was removed under reduced pressure, H2O (3 mL) was added and extracted with EtOAc (3 x 20 mL) and washed with H2O (2 x 20 mL, followed by brine (20 mL, The organic layer was dried (Na2SO4, and the solvent was distilled off to furnish a viscous mass which was purified by column chromatography over silica gel. Elution of the column with 20% EtOAc-hexane afforded the product 8a. Similarly, other compounds were synthesized. Compound 8a: white solid, mp 174°C. IR (KBr, 2918, 2899, 1643, 1600 cm-1. 1H NMR 400 MHz, CDCl3, δ, 3.6
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- The spectral data, especially NMR studies, showed that the OCH 2 protons appears as two separate singlets which is further supported by the DEPT experiment. DEPT contains two extra methylene groups due to the rapid interconversion of the existing possible conformers. Compound 10b: yellow solid, mp 250°C. IR (KBr, 2941, 2838, 1647, 1625 cm-1. 1H NMR (300 MHz, CDCl3, δ, 3.45-3.61 (m, 2 H, CHCH2, 3.80 (s, 3 H, OCH3, 4.89 (s, 1 H, OCHa, 5.44 (s, 1 H, OCHb, 6.74 (d, 1 H, J, 11.4 Hz, CHa, 7.11-7.15 (m, 1 H, CHb, 7.19-7.22 (m, 5 H, ArH, 7.43-7.54 (m, 4 H, ArH, 8.23 (d, 1 H, J, 7.5 Hz, ArH, 8.46 (d, 1 H, J, 3.2 Hz, ArH, 13C NMR 75 MHz, CDCl3, d, 31.6, 59.4, 109.2, 112.6, 112.7, 115.1, 119.2, 125.3, 125.8, 128.5, 128.9, 129.5, 136.0, 136.7, 138.8, 138.3, 154.1, 154.7, 159.8, 172.5, 194.6, TOF MS ES
- 3: C, 75.74; H, 5.08; N, 7.07. Found: C, 75.81; H, 5.03; N, 7.21.

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