Synthesis of β-carbolines from aldehydes and ketones via the α-siloxy α,β-unsaturated esters

Tetrahedron Letters

Volumn 51, Issue 33, 2010, Pages 4361-4364

  He, Shuwen ^a   Lai, Zhong ^a   Yang, David X ^a   Hong, Qingmei ^a   Reibarkh, Mikhail ^a   Nargund, Ravi P ^a   Hagmann, William K ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Ketoester; Siloxy , unsaturated ester; Carboline; Pictet Spengler reaction; Tryptamine

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA SILOXY ALPHA,BETA ESTER; BETA CARBOLINE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; TRYPTAMINE; TRYPTOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HORNER WADSWORTH EMMONS REACTION; PICTET SPENGLER REACTION; PRODUCTIVITY; SYNTHESIS;

EID: 77955423257     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.053     Document Type: Article

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19. 3, 500 MHz) δ = 0.083 (3H, s), 0.091 (3H, s), 0.902 (9H, s), 1.30 (9H, m), 4.21 (6H, m), 4.56 (1H, d, J = 18 Hz).
20. 3, 500 MHz) δ = 0.15 (6H, s), 0.97 (9H, s), 1.35 (3H, t, J = 7 Hz), 1.46 (2H, qd, J = 12 Hz, 4.5 Hz), 1.67 (2H, d, J = 12 Hz), 3.25 (1H, m), 3.48 (2H, t, J = 12 Hz), 3.96 (2H, d, J = 12 Hz), 4.25 (2H, q, J = 7 Hz), 5.33 (1H, d, J = 10 Hz).
21. 3OD, 500 MHz) δ = 1.26 (3H, t, J = 7 Hz), 1.26 (1H, m), 1.32 (1H, m), 1.39 (1H, d, J = 12.5 Hz), 1.65 (1H, d, J = 12.5 Hz), 1.84 (1H, m), 1.93 (1H, dd, J = 14 Hz, 5 Hz), 2.18 (1H, dd, J = 14 Hz, 6.5 Hz), 2.64 (1H, dt, J = 15 Hz, 3.1 Hz), 2.76 (1H, m), 3.13 (1H, m), 3.21 (1H, dq, J = 12 Hz, 3.1 Hz), 3.33 (2H, m), 3.76 (1H, d, J = 12 Hz), 3.84 (1H, d, J = 12 Hz), 4.19 (2H, m), 6.96 (1H, t, J = 8 Hz), 7.06 (1H, d, J = 8 Hz), 7.32 (1H, d, J = 8 Hz), 7.38 (1H, d, J = 8 Hz).
22. 3OD, 500 MHz) δ = 1.23 (3H, t, J = 7 Hz), 2.66 (1H, dt, J = 15 Hz, 3.9 Hz), 2.68 (1H, m), 3.04 (1H, m,), 3.10 (1H, m,), 3.14 (1H, d, J = 13.5 Hz), 3.54 (1H, d, J = 13.5 Hz), 4.17 (2H, dd, m), 6.93 (2H, d, J = 8 Hz), 6.98 (1H, d, J = 7.5 Hz), 7.10 (1H, t, J = 7.5 Hz), 7.38 (1H, d, J = 7.5 Hz), 7.41 (1H, d, J = 7.5 Hz), 7.58 (2H, d, J = 8 Hz).