The effect of an N-substituent on the recyclization of (2-aminoaryl)bis(5-tert-butyl-2-furyl)methanes: synthesis of 3-furylindoles and triketoindoles

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 20-24

  Butin, Alexander V ^a   Smirnov, Sergey K ^a   Trushkov, Igor V ^b  

^a KUBAN STATE TECHNOLOGICAL UNIVERSITY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

1,4 Diketone; Furan; Indole; Recyclization

Indexed keywords

ACETAMIDE DERIVATIVE; ACID; AMIDE; FURAN; INDOLE DERIVATIVE; KETONE DERIVATIVE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; RING OPENING; SYNTHESIS;

EID: 36549038036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.015     Document Type: Article

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32. 4, and evaporated under reduced pressure. The residue was dissolved in hexane, and the resultant solution was filtered through a pad of silica gel (5-40 μm), and evaporated under reduced pressure to dryness. The resulting yellow oil, 8b (12.44 g, 94%) was used as such in the next step.
33. 2/hexane mixture and filtered through a pad of silica gel (5-40 μm) and evaporated under reduced pressure to dryness. The obtained residue, 9b (4.78 g, 83%) was used as such in the next step.
34. Ts).
35. Ar).
36. +), 412 (29), 411 (100), 397 (23), 396 (81), 326 (12), 313 (15), 312 (70), 297 (14), 296 (33), 92 (18), 91 (34), 57 (53).
37. 3): δ 22.3, 26.4 (3C), 26.7 (3C), 30.8, 36.2, 36.6, 44.1 (2C), 56.1, 56.5, 94.6, 103.5, 113.5, 119.1, 128.9, 145.5, 146.2, 146.9, 195.3, 215.2, 217.8; MS (EI) m/z: 429 (36), 344 (14), 288 (13), 272 (10), 244 (12), 204 (16), 190 (15), 141 (85), 113 (48), 58 (100), 57 (54).
38. Refluxing of 11 in ethanolic HCl led to significant decomposition and, as a result, to lower yields of the reaction products.
39. 4 and evaporated to dryness. Compound 13b was isolated as described in Ref. 12. Yield of 13b (0.44 g, 43%).
40. +), 396 (42), 57 (70).
41. Transformation of 14b into 13b was performed analogously to the preparation of 13b from 11b (see Ref. 12).