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Volumn , Issue 16, 2008, Pages 2465-2470

Generation of arylcyclopenta-1,3-dienes from cyclopenteno-spiro- benzosultams: Synthesis of 2-arylnorbornenes

Author keywords

Alkylation; Cycloadditions; Cyclopentadienes; Extrusion; Hydrogen shift; Metathesis; Norbornene

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; HYDROGEN; NORBORNENE DERIVATIVE; SPIRO COMPOUND; SULFUR DIOXIDE; XYLENE;

EID: 54249098276     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078219     Document Type: Article
Times cited : (11)

References (20)
  • 15
    • 54249085058 scopus 로고    scopus 로고
    • Alkylation of Benzosultams with cis-1,4-Dichlorobut-2- ene, Typical Procedure Benzosultam 1 (2 mmol) and cis-1,4-dichlorobut-2-ene (280 mg, 2.4 mmol) in DMSO (5 mL) were stirred with solid powdered NaOH (1 g) at r.t. until the starting material disappeared (TLC control, hexane-EtOAc, 2:1, Then the reaction mixture was poured into H2O (50 mL, The product was filtered dissolved in CH 2Cl2 and dried over MgSO4. After evaporation of the solvent the product was recrystallized. The following compounds were obtained. 1,5-Dimethyl-1,3-dihydro-2,1-benzisothiazolo-3-spiro-4′- cyciopentene 2,2-Dioxide (2a) Yield 53, mp 107-109°C (from EtOH, colorless crystals. 1H NMR (500 MHz, CDCl3, δ, 2.30 (s, 3 H, 2.72, 3.57, 5.82 (AA′MM′XX′, J AM, 15.7 Hz, 6 H, 3.11 (s, 3 H, 6.61 (d, J, 8.0 Hz, 1 H, 7.02 d, J, 1.4 Hz, 1 H
    • AM = 16.7 Hz, 2 H), 3.20 (s, 3 H), 6.98 (dd, J = 7.9, 1.0 Hz, 1 H), 7.48 (dd, J = 8.1, 8.1 Hz, 1 H), 7.58
  • 16
    • 54249153443 scopus 로고    scopus 로고
    • 2 (5 mL) were stirred under argon atmosphere until the starting material disappeared (TLC control). After completion of the reaction the catalyst was removed by passing the reaction mixture through short silica gel column, and after evaporation of the solvent the products were purified by crystallization from EtOH. The following compounds were obtained: 2b (yield 85%) and 2e (yield 73%).
    • 2 (5 mL) were stirred under argon atmosphere until the starting material disappeared (TLC control). After completion of the reaction the catalyst was removed by passing the reaction mixture through short silica gel column, and after evaporation of the solvent the products were purified by crystallization from EtOH. The following compounds were obtained: 2b (yield 85%) and 2e (yield 73%).
  • 17
    • 54249149532 scopus 로고    scopus 로고
    • Cycloaddition of Arylcyclopentadienes to Dienophiles, General Procedure Spirocyclopentenosultam (2, 1 mmol) and dienophile (2 mmol) were refluxed in 1,2,4-trichlorobenzene (2 mL) for 15 min. The reaction mixture was subjected to column chromatography. Trichlorobenzene was eluted with hexane-EtOAc (100:1) and then the products were separated with hexane-EtOAc (4:1, The following compounds were formed: Compound 7: 1H NMR (500 MHz, DMSO-d6, δ, 1.64 (br d, J, 8.7 Hz, 1 H, 2.05 (br d, J, 8.7 Hz, 1 H, 2.17 (s, 3 H, 2.68 (d, J, 5.1 Hz, 3 H, 2.70 (dd, J, 9.8, 1.5 Hz, 1 H, 2.92 (dd, J, 9.8, 1.4 Hz, 1 H, 3.13 (m, 1 H, 3.31 (m, 1 H, 3.53 (s, 3 H, 3.57 (s, 3 H, 4.69 (q, J, 5.1 Hz, 1 H, 6.36 (d, J, 3.1 Hz, 1 H, 6.47 (br d, J, 8.3 Hz, 1 H, 6.85 (d, J, 1.8 Hz, 1 H, 6.92 (dd, J, 8.3, 1.8 Hz, 1 H, 13C NMR 125 MHz, DMSO-d6
    • 6,): δ = 1.64 (br d, J = 8.7 Hz, 1 H), 2.05 (br d, J = 8.7 Hz, 1 H), 2.17 (s, 3 H), 2.68 (d, J = 5.1 Hz, 3 H), 2.70 (dd, J = 9.8, 1.5 Hz, 1 H), 2.92 (dd, J = 9.8, 1.4 Hz, 1 H), 3.13 (m, 1 H), 3.31 (m, 1 H), 3.53 (s, 3 H), 3.57 (s, 3 H), 4.69 (q, J = 5.1 Hz, 1 H), 6.36 (d, J = 3.1 Hz, 1 H), 6.47 (br d, J = 8.3 Hz, 1 H), 6.85 (d, J = 1.8 Hz, 1 H), 6.92 (dd, J = 8.3, 1.8 Hz, 1 H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.