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Volumn , Issue 8, 2008, Pages 1208-1210

Synthesis of functionalized 5-oxo-2,5-dihydro-1H-pyrroles from primary alkylamines, oxalyl chloride, and dimethyl acetylenedicarboxylate

Author keywords

3 pyrroline 2 one; Acetylenic ester; Alkylamines; Enaminone; Multicomponent reaction; Oxalyl chloride

Indexed keywords

5 OXO 2,5 DIHYDRO 1H PYRROLE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALIPHATIC AMINE; CHLORIDE; OXALYL CHLORIDE; PYRROLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 44449102191 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072657 Document Type: Article

Times cited : (15)

References (16)

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16
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- Dimethyl 1-Benzyl-2,4-dihydroxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate (4a) To a stirred solution of DMAD (0.34 g, 2.4 mmol) and alkylamine (0.20 g, 2 mmol) in CH2Cl2 (10 mL) was added oxalyl chloride (0.17 mL, 2 mmol) at r.t. The reaction mixture was then stirred for 24 h. The solvent was removed under reduced pressure and the precipitate was purified by recrystallization from Et2O to give 4a. Compound 4a: white powder; 170-171°C (decomp, yield 0.57 g (90, IR (KBr, νmax, 3360, 3135, 1741, 1705, 1674, 1425, 1311 cm-1. 1H NMR (500.1 MHz, CDCl3, δ, 3.19 (3 H, s, OMe, 3.73 (3 H, s, OMe, 4.28 (1 H, d, 3J, 15.5 Hz, CH, 4.77 (1 H, br s, OH, 4.80 (1 H, d, 3J, 15.5 Hz, CH, 7.24-7.30 (5 H, m, CH, 9.09 (1 H, br s, OH) ppm. 13C NMR (125.7 MHz, CDCl3, δ, 42.7 NCH2, 51.8
- +], 262 (70), 244 (100), 91 (50), 77 (64).

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