One-pot synthesis of furo[3,4-b]pyridin-5(7h)-ones from 2-bromopyridine-3-carboxylic acid and carbonyl compounds

Synthesis

Volumn , Issue 18, 2009, Pages 3026-3028

  Kobayashi, Kazuhiro ^a   Kozuki, Taketoshi ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

2 bromopyridine 3 carboxylic acid; Bromine lithium exchange; Furopyridinones; Lactonization; Lithium 2 lithiopyridine 3 carboxylate

Indexed keywords

2-BROMOPYRIDINE-3-CARBOXYLIC ACID; AFTER-TREATMENT; BUTYLLITHIUM; CARBONYL COMPOUNDS; FUROPYRIDINONES; LACTONIZATION; ONE-POT METHOD; ONE-POT SYNTHESIS;

BROMINE; CARBONYLATION; CARBOXYLATION; CARBOXYLIC ACIDS; HYDROCHLORIC ACID; LITHIUM; ORGANIC ACIDS;

LITHIUM COMPOUNDS;

3',4',5',6' TETRAHYDRO 5H SPIRO[FURO[3,4 B]PYRIDINE 7,2' PYRAN] 5 ONE; 4 METHYL 5'H SPIRO[CYCLOHEXANE 1,7' FURO[3,4 B]PYRIDIN] 5' ONE; 4 TERT BUTYL 5'H SPIRO[CYCLOHEXANE 1,7' FURO[3,4 B]PYRIDIN] 5' ONE; 4,5 DIHYDRO 3H,5'H SPIRO[FURAN 2,7' FURO[3,4 B]PYRIDIN] 5' ONE; 5'H SPIRO[CYCLOHEXANE 1,7' FURO[3,4 B]PYRIDIN] 5' ONE; 5'H SPIRO[CYCLOOCTANE 1,7' FURO[3,4 B]PYRIDIN] 5' ONE; 5'H SPIRO[CYCLOPENTANE 1,7' FURO[3,4 B]PYRIDIN] 5' ONE; 7 ISOPROPYLFURO[3,4 B}PYRIDIN 5(7H) ONE; 7 TERT BUTYL 7 METHYLFURO[3,4 B]PYRIDIN 5(7H) ONE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HYDROCHLORIC ACID; LITHIUM DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLIZATION; ONE POT SYNTHESIS; SUBSTITUTION REACTION; TEMPERATURE;

EID: 70449434888     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216894     Document Type: Article

References (7)

1. Generation of lithium 2-lithiobenzoate from 2-bromoben-zoic acid has been reported by Parham et al.: Parham, W. E.; Piccirilli, R. M. J. Org. Chem. 1976, 41, 1268.
2. Its applications to the synthesis of phthalides have also been reported: Parham, W. E.; Egberg D. C.; Sayed, Y. A.; Thrrailkill, R. W.; Kaeyser, G. E.; Neu, M.; Montgomery, W. C.; Jones, L. D. J. Org. Chem. 1976, 41 2628.
3. Pirkle, W. H.; Sowin, T. J. J. Org. Chem. 1987, 52, 3011.
4. Canonne, P.; Lemay, G.; Belanger, D. Tetrahedron Lett. 1980, 21, 4167.
5. Kende, A. S.; Veits, J. E.; Lorah, D. P.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 2423.
6. van Bergman, T. J.; Kellogg, R. M. J. Am. Chem. Soc. 1972, 94, 8451.
7. 2O or DME in place of THF.