Gold-facilitated '6-exo-dig' intramolecular cyclization of 2-[(2-nitrophenyl)ethynyl]phenylacetic acids: General access to 5H-benzo[b]carbazole-6,11-diones

Synlett

Volumn , Issue 19, 2009, Pages 3107-3110

  Salas, Cristian O ^a   Reboredo, Francisco J ^b   Estévez, Juan C ^b   Tapia, Ricardo A ^a   Estévez, Ramón J ^b  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alkynes; Annulations; Fused ring systems; Gold(I) chloride; Indoles; Lactones; Nitro compounds; Quinones

Indexed keywords

2 [(2 NITROPHENYL)ETHYNYL]PHENYLACETIC ACID DERIVATIVE; 5H BENZO[B]CARBAZOLE 6,11 DIONE DERIVATIVE; CARBAZOLE DERIVATIVE; GOLD; PHENYLACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 72149096833     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218362     Document Type: Article

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31. 2)
32. 3N (5 mL) was first added, then TMS-acetylene (3.60 mmol) was slowly added and the resulting mixture was stirred at room temperature for 1.5 h for 6a or 12 h for 6b. The solids were filtered off through a Celite pad, the solvents were removed in vacuo, and the crude oil was poured into water and extracted with methylene chloride. The pooled organic liquids were washed with brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. Compound 6a or 6b were isolated by flash column chromatography.
33. 3N (5 mL) was first added, then a solution of 6a or 6b (3.85 mmol) in anhydrous THF (10 mL) was slowly added and the resulting mixture was stirred at room temperature for 12 h. The solids were filtered off through a Celite pad, the solvents were removed in vacuo and the filtrate was concentrated to dryness in vacuo. Compound 7a or 7b were isolated by flash column chromatography.
34. 3 (0.10 equiv), acetonitrile (2 mL/0.4 mmol) was added under argon. The solution was purged with argon three times and then AuCl (0.10 equiv) was added. After stirring at room temperature for 12 h, the reaction mixture was filtered through a Celite pad and liquids from the filtrate were removed under reduced pressure. Flash column chromatography of the crude material allowed compound 2a or 2b to be isolated.
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