478488-15-2Relevant academic research and scientific papers
Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines
Belanger, Guillaume,Hong, Fang-Tsao,Overman, Larry E.,Rogers, Bruce N.,Tellew, John E.,Trenkle, William C.
, p. 7880 - 7883 (2002)
The construction of triazacyclopenta[cd]pentalene diesters 6 by the reaction of dihydropyrrole α-ketoesters 3 with acylated hydrazines was evaluated further as a potential central strategic step in the total syntheses of complex guanidine alkaloids such as palau'amine and styloguanidine. Successful cyclocondensations were realized with acid-stable 2,2,2-trichloroethyl carbazate and thiosemicarbazide, but not tert-butyl carbazate. The substituent on the pyrrolidine nitrogen can be alkoxycarbonyl, sulfonyl, or an N-alkyl-2-acylpyrrole group. Siloxy substitution at C1 of the α-ketoester side chain is also tolerated.
