Abstract
A general and practical route has been considered for the synthesis of stable heterocyclic phosphorus ylides by a one-pot condensation reaction between dialkyl acetylenedicarboxylates and triphenylphosphine in the presence of -SH or -NH heterocyclic compounds such as 5mercapto-1-methyltetrazole or 5-aminotetrazole. The stable ylides involving 4d-e exist in solution as a mixture of two isomers, while 4a-c indicate only one isomer. Dynamic parameters
Highlights
The synthesis of phosphorus ylides is important in organic chemistry because of their application in the synthesis of organic products,[1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19] and especially the synthesis of naturally occurring products with biological and pharmacological activity.[20,21,22,23,24] Phosphorus ylides are usually prepared by deprotonation of phosphonium salts, which can be prepared most often by the reaction of triphenylphosphine and an alkyl halide.[1,2,3] In recent years a three- component method has been developed 25-28 for the synthesis of organophosphorus compounds using a novel approach employing vinylphosphonium salts
The reaction between triphenylphosphine and dialkyl acetylenedicarboxylates 1 led to the zwitterion 2, which was followed by attack by the nitrogen anion of the 5-aminotetrazole, or sulfur anion of the 5-mercapto-1-methyltetrazole, to generate the phosphorus ylides E-4 and Z-4
The 1H, 13C and 31P NMR spectra of the crude products clearly indicated the formation of the phosphorus ylides 4
Summary
The synthesis of phosphorus ylides is important in organic chemistry because of their application in the synthesis of organic products,[1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19] and especially the synthesis of naturally occurring products with biological and pharmacological activity.[20,21,22,23,24] Phosphorus ylides are usually prepared by deprotonation of phosphonium salts, which can be prepared most often by the reaction of triphenylphosphine and an alkyl halide.[1,2,3] In recent years a three- component method has been developed 25-28 for the synthesis of organophosphorus compounds using a novel approach employing vinylphosphonium salts. (i) Reaction between triphenylphosphine, dialkyl acetylenedicarboxylate 1 (1a, 1b or 1c) and 5-aminotetrazole or 5-mercapto-1-methyltetrazole 3 for generating stable phosphorus ylides 4a-e.
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