A convenient Fischer indole synthesis of 2,3′-biindoles

Tetrahedron Letters

Volumn 52, Issue 21, 2011, Pages 2642-2644

  Alford, Philip E ^a   Fu, Liangfeng ^a   Kubert, Joseph K ^a   Wang, Lingshan ^a   Gribble, Gordon W ^a  

^a Lamont Doherty Earth Observatory   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3' BIINDOLE DERIVATIVE; 3 ACYLINDOLE DERIVATIVE; 4 NITROPHENYLHYDRAZINE; ANCORINAZOLE; ANION; CARBAZOLE DERIVATIVE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; INDIRUBIN; INDOLE DERIVATIVE; NATURAL PRODUCT; OLIGOMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; DRUG ISOLATION; FISCHER TROPSCH SYNTHESIS; HYDROLYSIS; ISATIS INDIGOTIN; MOLECULAR STABILITY; OLIGOMERIZATION; PROTON TRANSPORT; SUPRAMOLECULAR CHEMISTRY;

EID: 79955466297     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.049     Document Type: Article

References (48)

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33. Representative procedure: A solution of phenylhydrazine hydrochloride (75 mg, 0.52 mmol), 3-acetyl-1-(phenylsulfonyl)indole (150 mg, 0.5 mmol), and acetic acid (3 drops, 0.15 mL) in anhydrous ethanol (2 mL) over molecular sieves (3 ) was brought to reflux for 2 h and monitored by TLC. When conversion to 14 was complete, after 8 h, the solvent was removed by rotary evaporation. Toluene (3 mL) and PPA (1 mL) was added without removing molecular sieves and the reaction mixture was brought to reflux and monitored by TLC. After 3 h, TLC showed complete conversion. The reaction mixture was neutralized using sat aq sodium bicarbonate solution, extracted with DCM, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting brown oil was purified by column chromatography over silica gel (1:1 hexanes/DCM) to produce product 15 as a solid (116 mg, 62%).
34. 2S: 375.0929. Found: 375.0919.
35. 2S: 372.0933. Found: 372.0931.
36. 2SF: 390.0838. Found: 390.0837.
37. 4S: 434.1049. Found: 434.1049.
38. 3) δ 138.2, 136.4, 135.3, 134.4, 129.9, 129.7, 129.6, 127.1, 126.7, 125.6, 124.6, 124.2, 122.7, 121.1, 119.9, 119.2, 115.9, 114.2, 111.1, 110.4, 10.0.
39. 2FS: 404.0995. Found: 404.0980.
40. 4S: 448.1205. Found: 448.1220
41. 2S: 448.1246. Found 448.1237
42. 2SF: 466.1151. Found 466.1145.
43. 3S: 478.1351. Found: 478.1359.
44. 4S: 510.1362. Found: 510.1373.
45. 3) δ 138.1, 135.3, 135.2, 134.7, 134.2, 130.2, 130.0, 129.6, 128.7, 128.6, 127.1, 126.8, 126.5, 125.5, 125.3, 124.7, 124.0, 121.1, 119.4, 115.7, 114.0, 110.9, 21.8.
46. 3) δ 9.08 (br s, 1H), 8.86 (br s, 1H), 7.99 (m, Hz), 7.58 (m, 1H), 7.46 (m, 1H), 7.33 (m, 1H), 7.17-7.23 (m, 2H), 7.04-7.14 (m, 2H), 6.75 (m, 1H).
47. 3: 249.1266. Found: 249.1268.
48. 3) δ 145.3, 138.1, 138.1, 136.0, 134.6, 129.6, 129.6, 128.4, 127.0, 125.7, 124.6, 124.4, 124.4, 123.3, 120.5, 113.5, 113.4, 13.3.