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A Convenient Method for the Synthesis of Insect Growth Regulators Cyclopentene Analogs of Alkyl (2 E ,4 E )‐Dodecadienoates
Author(s) -
Novák Lajos,
Rohály János,
Gálik György,
Fekete Jenö,
Varjas László,
Szántay Csaba
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860309
Subject(s) - chemistry , yield (engineering) , cyclopentene , wittig reaction , cyclopentenone , methyl vinyl ketone , alkyl , ketone , organic chemistry , salt (chemistry) , medicinal chemistry , catalysis , materials science , metallurgy
Starting with the aldehydes 7 and methyl vinyl ketone the title compounds 3a – d and their corresponding 2 Z isomers 16a – d are prepared in three steps: (1) thiazolium salt‐catalyzed addition reaction to yield the diketone 8 , (2) cyclocondensation reaction to give the corresponding cyclopentenone 11 , and (3) Wittig‐Horner reaction. This procedure is used to synthesize the 5‐substituted 2,4‐pentadienoates 3f – i . The results from pesticide screening are also reported.