Synthesis of Chromeno[3,4- b ]pyrrol-4(3 H)-ones by Cyclocondensation of 1,3-Bis(trimethylsilyloxy)buta-1,3-dienes with 4-Chloro-3-nitrocoumarin

Synlett

Volumn , Issue 10, 2010, Pages 1533-1535

  Fatunsin, Olumide ^a   Iaroshenko, Viktor O ^a,b   Dudkin, Sergii ^a   Shkoor, Mohanad ^a   Volochnyuk, Dmitro ^b,c   Gevorgyan, Ashot ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c ENAMINE LTD   (Ukraine)

Author keywords

Coumarin; Cyclization; Heterocycles; Pyrroles; Silyl enol ethers

Indexed keywords

CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; LAMELLARIN D; METHYL 2 (1 ETHYL 3,4 DIHYDRO 4 OXOCHROMENO[3,4B]PYRROL 2YL) ACETIC ACID; METHYL 2 (3,4 DIHYDRO 1 METHYL 4 OXOCHROMENO[3,4B]PYRROL 2YL) ACETIC ACID; METHYL 4 (3 NITRO 2 OXO 2H CHROMEN 4 YL) 3 OXOHEXANOIC ACID; METHYL 4 (3 NITRO 2 OXO 2H CHROMEN 4 YL) 3 OXOPENTANOIC ACID; NINGALIN B; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; STOICHIOMETRY; X RAY ANALYSIS;

EID: 77953259618     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1220068     Document Type: Article

References (12)

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2. Yu D L., Suzuki M, Xie L, Morris-Natschke S L., Lee K H., Med. Res. Rev. 2003 23 322
3. Fylaktakidou K C., Hadjipavlou-Litina D J., Litines K E., Nicolaides D N., Curr. Pharm. Res. 2004 10 3813
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5. Chen L, Xu M H., Adv. Synth. Catal. 2009 351 2005; and references 2-5 cited therein
6. For a review, see:, Langer P, Synthesis 2002 441
7. 4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, heptanesEtOAc) to give 5ak.
8. 7: 56.43; H, 4.08; N, 4.39. Found: C, 56.94; H, 4.36; N, 4.21.
9. 7: C, 57.66; H, 4.51; N, 4.20. Found: C, 57.52; H, 4.50; N, 4.16.
10. 2 was consumed, the mixture was stirred for 3 d at 20 C (TLC control). The reaction mixture was filtered through a Celite pad (23 cm). The Celite was washed 3 times with MeOH. The solvent of the filtrate was removed under reduced pressure. The residue was purified by preparative chromatography (silica gel, heptanesEtOAc).
11. +: 272.0917; found: 272.0923.
12. +: 286.1074; found: 286.1076.