89882-71-3Relevant academic research and scientific papers
The optimization for cyclization reaction of 2-(2-carbomethoxyethynyl) aniline derivatives and formal synthesis of pyrroloquinoline quinone and its analogue utilizing a sequential coupling-cyclization reaction
Hiroya, Kou,Matsumoto, Shigemitsu,Ashikawa, Masayasu,Kida, Hitomi,Sakamoto, Takao
, p. 12330 - 12338 (2007/10/03)
The reaction conditions for the Pd-catalyzed cyclization reaction of 2-(2-carbomethoxyethynyl)aniline derivatives were investigated. The amounts of Pd(PPh3)4, methyl propiolate, and ZnBr2 could be significantly reduced compared with those reported in our preliminary publication by careful tuning of the solvent and the reaction temperature. In addition to the above results, formal syntheses of pyrroloquinoline quinone (PQQ) and its analogue from 2-amino-5-nitrophenol using a Pd-complex-catalyzed sequential coupling-cyclization reaction between methyl propiolate and 2-iodoaniline derivatives are described.
SYNTHESIS OF THE BACTERIAL COENZYME METHOXATIN
MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
, p. 3259 - 3268 (2007/10/02)
A short total synthesis of the bacterial coenzyme methoxatin (1) (4,5-dihydro-4,5-dioxo-1H-pyrroloquinoline-2,7,9-tricarboxylic acid) is described.The route involves the two step conversion of 4-acetamido-2-benzyloxybenzaldehyde (5b) into methyl 6-acetamido-4-benzyloxyindole-2-carboxylate (7b) (74percent), followed by regioselective annulation of the third ring (55percent), and debenzylation and oxidation with benzoyl t-butyl nitroxide to give the tricyclic quinone triester (13) (methoxatin triester) (83percent).
Synthesis of the Bacterial Coenzyme Methoxatin
MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
, p. 1372 - 1373 (2007/10/02)
A short synthesis of the bacterial coenzyme methoxatin, based on the thermolysis of the azide (3) to give the indole (4) and the regioselective formation of the pyrroloquinoline (5), is described.
