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Synlett
Volumn , Issue 1, 2008, Pages 0025-0028
Intramolecular ring-opening reactions of 1-(2-methoxyphenyl)-6- oxabicyclo[3.2.0]heptanes: spirocyclic dihydrobenzofurans from fused bicyclic oxetanes
Author keywords

Cyclizations; Heterocycles; Lewis acids; Neighboring group effects; Spiro compounds
Indexed keywords

BENZOFURAN DERIVATIVE; CHLORIDE; FURETHIDINE; HEPTANE DERIVATIVE; HYDROCHLORIC ACID; LEWIS ACID; OXETANE DERIVATIVE;
EID: 38549127139     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990921     Document Type: Article
Times cited : (9)
References (32)
  • 1
    • 0003607021 scopus 로고    scopus 로고
    • Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Padwa, A, Eds, Elsevier: Oxford
    • Linderman, R. J. In Comprehensive Heterocyclic Chemistry II, Vol. 1B; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Padwa, A., Eds.; Elsevier: Oxford, 1996.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 B
    • Linderman, R.J.1
  • 11
    • 0026721268 scopus 로고    scopus 로고
    • N2 displacement at C-20 leading to the formation of tetrahydrofurans: (a) Farina, V.; Huang, S. Tetrahedron Lett. 1992, 33, 3979.
    • N2 displacement at C-20 leading to the formation of tetrahydrofurans: (a) Farina, V.; Huang, S. Tetrahedron Lett. 1992, 33, 3979.
  • 21
    • 38549139357 scopus 로고    scopus 로고
    • Typical Experimental for Oxetane Ring-Opening Reaction with HCl To a solution of oxetane 1a (50 mg, 0.18 mmol) in Et2O (5 mL) at 0°C HCl (1 M in Et2O, 1.80 mL, 1.80 mmol) was added over a period of 10 min. The resulting solution was stirred for 18 h at r.t. The resulting mixture was poured into H2O (10 mL) and the aqueous layer was extracted with Et2O (2 x 10 mL, The combined organic phases were washed with brine (10 mL, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified via column chromatography (hexane-EtOAc, 8:2) to furnish spirocycle 8a as a colorless oil (37 mg, 78, Rf, 0.2 (hexane-EtOAc, 8:2, mp 88-90°C. IR (neat, νmax, 3445, 2945, 2865, 1651, 1497, 1466, 1199 cm-1. 1H NMR (360 MHz, CDCl3, δ, 6.65 (1 H, s, CCHCOCH3, 6.58 1 H, s, CH2OCCHCCH 3
    • +], 231 (5), 205 (33), 192 (6), 175 (33), 163 (9).
  • 22
    • 38549115409 scopus 로고    scopus 로고
    • Typical Experimental Procedure for Oxetane Ring-Opening Reaction with AcCl To a solution of oxetane 1a (50 mg, 0.18 mmol) in DCE (10 mL) at r.t, AcCl (0.13 mL, 1.80 mmol) was added. The resulting solution was stirred overnight at r.t. poured into H2O (10 mL) and the aqueous layer was extracted with CH2Cl2 (2 x 10 mL, The combined organic phases were dried over MgSO4, filtered, and reduced in vacuo. The crude product was purified via column chromatography (hexane-EtOAc, 9:1) to furnish spirocycle 9a as a colorless oil (45 mg, 81, R f, 0.2 (hexane-EtOAc, 9:1, IR (neat, νmax, 2950, 2869, 2252, 2105, 1739, 1651, 1490, 1464, 1223, 1047 cm-1. 1H NMR (360 MHz, CDCl3, δ, 6.66 (1 H, s, CCHCOCH3, 6.54 (1 H, s, CH2OCCHCCH 3, 4.96 (1 H, dd, J, 6.8, 1.6 Hz, CHOCOCH 3, 4.45 1 H, d
    • +], 262 (21), 175 (66), 160 (8), 115 (8), 91 (7), 69 (5), 43 (16).
  • 27
    • 37049112241 scopus 로고    scopus 로고
    • N2-type ring opening of the activated ether with chloride nucleophile, where the regiochemical outcome is presumably a result of the preferred attack by chloride at a secondary carbon over a primary neopentyl-like carbon. For an analogous example in oxetane ring opening using HCl, see: Ceccherelli, P.; Curini, M.; Marcotullio, M. C. J. Chem. Soc., Perkin Trans. 1 1985, 2173.
    • N2-type ring opening of the activated ether with chloride nucleophile, where the regiochemical outcome is presumably a result of the preferred attack by chloride at a secondary carbon over a primary neopentyl-like carbon. For an analogous example in oxetane ring opening using HCl, see: Ceccherelli, P.; Curini, M.; Marcotullio, M. C. J. Chem. Soc., Perkin Trans. 1 1985, 2173.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.