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Volumn 6, Issue 11, 1998, Pages 2103-2110

Synthesis and structure-activity data of some new epibatidine analogues

Author keywords

Epibatidine analogues; High pressure; Hydroarylation; Structure activity data

Indexed keywords

ALKALOID; EPIBATIDINE; EPIBATIDINE DERIVATIVE; NICOTINIC RECEPTOR; UNCLASSIFIED DRUG;

EID: 0031739373     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00163-1     Document Type: Article
Times cited : (42)

References (46)
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    • Similarly, N-carbomethoxy 2,4-dimethylpyrrole gave a high-pressure Diels-Alder reaction with phenyl vinyl sulfone in chloroform at 12 kbar and 50 °C to yield the crude sulfonyl compound after 48 h. Subsequent reductive desulfonylation with 6% sodium amalgam gave 1,3-dimethyl-7-carbomethoxy-7-azabicyclo[2.2.1]hept-2-ene in ca. 35% isolated yield.
    • Similarly, N-carbomethoxy 2,4-dimethylpyrrole gave a high-pressure Diels-Alder reaction with phenyl vinyl sulfone in chloroform at 12 kbar and 50 °C to yield the crude sulfonyl compound after 48 h. Subsequent reductive desulfonylation with 6% sodium amalgam gave 1,3-dimethyl-7-carbomethoxy-7-azabicyclo[2.2.1]hept-2-ene in ca. 35% isolated yield.
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    • 1H NMR δ 1.58 (2H, br s), 2.65 (1H, m), 3.12 (1H, br s), 3.36 (1H, br d), 3.66 (3H, s, OMe), 4.70 (1H, d), 6.29 (2H, br d). Formation of 6-azabicyclo[3.1.1]hept-2-ane derivatives have been described before in literature, see for example: Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. Structure elucidation and application of 4′ towards epibatidine-type compounds will be described in a forthcoming paper.
    • 1H NMR δ 1.58 (2H, br s), 2.65 (1H, m), 3.12 (1H, br s), 3.36 (1H, br d), 3.66 (3H, s, OMe), 4.70 (1H, d), 6.29 (2H, br d). Formation of 6-azabicyclo[3.1.1]hept-2-ane derivatives have been described before in literature, see for example: Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. Structure elucidation and application of 4′ towards epibatidine-type compounds will be described in a forthcoming paper.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.