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0344730734
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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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35
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0027442712
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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.
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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.
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For preparation of some aryl halides see: (a) 5-iodo-2-aminopyrimidine 6 from 2-aminopyrimidine:
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