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Volumn , Issue 11, 2009, Pages 1830-1834

Organocatalytic nucleophilic ring opening of cyclopropanecarbaldehydes by benzenethiols: Tandem synthesis of benzo[b]thiepines

Author keywords

Aldol reactions; Heterocycles; Regioselectivity; Ring opening; Tandem reactions

Indexed keywords

2 PHENYLCYCLOPROPANECARBALDEHYDE; 2 THIOSALICYLALDEHYDE; 2,3 DIHYDROBENZO[B]THIEPINE 4 CARBALDEHYDE; ALDEHYDE DERIVATIVE; BENZOTHIEPIN DERIVATIVE; BENZOTHIOPHENE; BUTYRALDEHYDE; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; ENAMINE; FLUORINE; LEWIS ACID; NITROBENZOIC ACID DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

EID: 67649958225     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217370     Document Type: Article
Times cited : (31)

References (48)
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    • 13C NMR, and MS).
    • 13C NMR, and MS).
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    • +.
    • +.
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    • Typical procedure for the tandem synthesis of benzo[b]-thiepines 6 was operated as described in ref. 14, except for replacing benzenethiols 2 with o-salicylaldehydes 5. The reaction gave 6 as off-white crystal solids. All new compounds have been isolated in pure form and characterized by spectral data (1H NMR, 13C NMR, and MS, Selected Data for Compounds 6 Compound 6e: yield 56, mp 120, 121 °C. 1H NMR (400 MHz, CDCl 3, δ, 9.62 (1 H, s, CHO, 7.40, 6.84 (8 H, m, ArH, and CH=C, 4.26 (1 H, dd, J, 3.2, 11.4 Hz, SCH, 3.79 (3 H, s, OCH 3, 3.26, 3.02 (2 H, m, CH2, 2.37 (3 H, s, CH 3, 13C NMR 100 MHz, CDCl3, δ, 194.9, 159.0, 150.4, 141.8, 137.5, 136.0, 135.2, 134.7, 134.5, 132.9, 130.9, 128.0, 114.2, 55.4, 52.6, 37.3, 21.0. ESI-HRMS: m/z calcd for C 19H18O2S: 310
    • 2S: 310.1028; found: 310.1031.
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    • For comparision, we also conducted the tandem reaction with the 'best' substrate 1c under Anand's condition (ref. 12). After refuxing in EtOH for 3 h, the reaction afforded a mixture of products, from which 6g was isolated in 13% yield.
    • For comparision, we also conducted the tandem reaction with the 'best' substrate 1c under Anand's condition (ref. 12). After refuxing in EtOH for 3 h, the reaction afforded a mixture of products, from which 6g was isolated in 13% yield.
  • 46
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    • Enantiomeric excess was determined chromatographically as follows: Diacel CHIRALPAK AS-H, hexane - 2-PrOH (80:20), flow rate 0.6 mL/min, λ = 254 nm.
    • Enantiomeric excess was determined chromatographically as follows: Diacel CHIRALPAK AS-H, hexane - 2-PrOH (80:20), flow rate 0.6 mL/min, λ = 254 nm.
  • 47
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    • 2 - n-hexane. Crystallographic data have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 726088.
    • 2 - n-hexane. Crystallographic data have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 726088.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.