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Synthesen, chemische Reaktionen und NMR‐spektroskopische Untersuchungen substituierter Phosphonopyruvate
Author(s) -
Feistauer Helmut,
Neidlein Richard
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780715
Subject(s) - chemistry , tautomer , oxime , substituent , enol , alkane stereochemistry , medicinal chemistry , stereochemistry , diamine , keto–enol tautomerism , organic chemistry , crystal structure , catalysis
Phosphonopyruvates: Syntheses, NMR Investigations, and Reactions The new 3‐(diethoxyphosphoryl)‐2‐oxopropanoates 5–24 and ‐propanamides 25–38 with various substituents at C(3) were prepared in moderate‐to‐good yields ( Schemes 2 and 3, Tables 1 and 2 ). It was shown that they adopt a preferred conformation in which the diethoxyphosphoryl group and the substituent at C(4) are antiperiplanar to each other (see B ). The keto‐enol tautomerization of phosphonopyruvates with PhC(3) (see 20 ) and MeSC(3) (see 24 and 33 ) was examined. In CHCl 3 , two tautomeric species exist, whereas in dimetylsulfoxide (DMSO), three tautomeric forms are observed. Oxime ethers, an oxime, and a phenylhydrazone of unsubstituted phosphonopyruvates were prepared (see 40–44 ), and quinoxalin‐2(1 H )‐ones could be obtained from the reaction of pyruvates with 4,5‐dimethylbenzene‐1,2‐diamine (see 45–47 ).