Palladium-catalyzed cyclization of 2-heteroyl-1-methylene-1,2,3,4-tetrahydroisoquinolines. Studies on 6-endo- versus 5-exo-trig cyclization

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1057-1060

  Bombrun, Agnès ^a   Sageot, Olivia ^a,b  

^a Laboratoire GlaxoWellcome   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02511-7     Document Type: Article

References (21)

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17. 4. Procedure of cyclization (entry 1, table 1): a mixture of enamide and catalyst system in dry solvent was boiled under reflux for 2-12 hours. After completion of the reaction the solvent was evaporated in vacuo. The residue was extracted with dichloromethane. After washing with a saturated aqueous solution of ammonium chloride, the combined organic extracts were dried over sodium sulfate and concentrated.
18. 3, 250 MHz) δ 9.5 (s, 1H), 8.55 (d, J = 8.0 Hz, 1H), 7.22 (d, J = 8.0 Hz, 1H), 7.2 (s, 1H), 6.7 (d, 2H), 4.2 (tr, 2H), 3.9 (s, 3H), 3.85 (s, 3H), 2.9 (tr, 2H)). (equation presented)
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