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Volumn 63, Issue 8, 2007, Pages 1775-1789

Regioselective construction of six-membered fused heterocyclic rings via Pd/C-mediated C-C coupling followed by iodocyclization strategy: a new entry to 2H-1,2-benzothiazine-1,1-dioxides

Author keywords

2H Benzo e 1,2 thiazine 1,1 dioxides; o Halobenzenesulfonamide; Palladium catalyst; Terminal alkynes

Indexed keywords

4 IODO 2H 1,2 BENZO[E][1,2]THIAZINE 1,1 DIOXIDE; ACETONITRILE; ALKYL GROUP; ALKYNE; BENZENE; BENZENESULFONAMIDE DERIVATIVE; BENZOTHIADIAZINE DERIVATIVE; BROMIDE; CARBON; FUSED HETEROCYCLIC RINGS; HYDROXYL GROUP; IODIDE; IODINE; O (1 ALKYNYL)ARENESULFONAMIDE; O HALOBENZENESULFONAMIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONAMIDE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33846263624     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.040     Document Type: Article
Times cited : (46)

References (75)
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    • Our interest stems from the fact that in 1992 one of us (MP) observed that iodocyclization of o-(1-alkynyl)benzoic acid, generated in situ under Sonogashira conditions, in the presence of ICl afforded the corresponding 3-iodo substituted ylidenephthalide, see:
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    • note
    • 3 with Z=2. The intensity data have been collected on Rigaku AFC-7S diffractometer with Mercury CCD area detector using graphite monochromatic Mo Kα radiation. The structure has been solved with direct methods and refined using least squares procedure using the Crystal Structure software. The present R factors are R1=0.034 and Rw=0.42. The number of observed reflections is 3420. Crystallographic data (excluding structure factors) for 8m have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 620161.
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    • note
    • (a) This behavior, which is not clear at this stage, perhaps could be ascribed to the structural features of the starting sulfonamide, was different from the previously reported cyclizations of the sulfoximine, which invariably led to the mixture of regioisomeric five and six-membered ring products, see Ref. 19; (b) Recently, the intramolecular cyclization of alkynylamides has been studied by Larock et al., which mainly produced isoindolin-1-ones in the presence of iodine, see Ref. 9.
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    • note
    • 3 in acetonitrile at 25 °C for 16 h.{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.