Conversion of 4-oxoproline esters to 4-substituted pyrrole-2-carboxylic acid esters.
The Grignard, Wittig, Tebbe, Horner-Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.
Arakawa
Yasushi
Y
Hokuriku University, Kanazawa, Japan. ya-arakawa@hokuriku-u.ac.jp
Yagi
Naomi
N
Arakawa
Yukimi
Y
Tanaka
Ken-ichi
K
Yoshifuji
Shigeyuki
S
D000478:Alkylation; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010675:Pheromones / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*
D007202:Indicators and Reagents; D010675:Pheromones; D011761:Pyrrolidonecarboxylic Acid