Regioselective Preparation of Diethyl 3,4-Disubstituted 1,5-Dihydro-5-oxo-2H-pyrrol-2-ylphosphonates and Their Coupling with Aldehydes. Application to the Synthesis of C/D-Rings Component of Phycocyanobilin | Zendy

Hla Ngwe | Zendy; Hideki Kinoshita | Zendy; Katsuhiko Inomata | Zendy

Open Access

Regioselective Preparation of Diethyl 3,4-Disubstituted 1,5-Dihydro-5-oxo-2H-pyrrol-2-ylphosphonates and Their Coupling with Aldehydes. Application to the Synthesis of C/D-Rings Component of Phycocyanobilin

Author(s) -

Hla Ngwe,

Hideki Kinoshita,

Katsuhiko Inomata

Publication year - 1994

Publication title -

bulletin of the chemical society of japan

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.145

H-Index - 99

eISSN - 1348-0634

pISSN - 0009-2673

DOI - 10.1246/bcsj.67.3320

Subject(s) - chemistry , regioselectivity , coupling (piping) , medicinal chemistry , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , mechanical engineering , engineering

Diethyl 3,4-disubstituted 1,5-dihydro-5-oxo-2H-pyrrol-2-ylphosphonates were regioselectively prepared by acidic hydrolysis of diethyl 3,4-disubstituted 5-bromo-2-pyrrolylphosphonates. The resulting 1,5-dihydro-2H-pyrrol-2-ones readily underwent the coupling reaction with various aldehydes to afford the corresponding 1,5-dihydro-5-methylene-2H-pyrrol-2-ones including pyrromethenone derivatives in good yields. A series of these reactions was successfully applied to the synthesis of C/D-rings component of phycocyanobilin

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