Pyrroloquinoline

Pyrrolo[3,2-6]pyrrole, N,N -dimethyl-UV spectra, 4, 1044 Pyrrolo[3,2-6]pyrrole, octahydro-synthesis, 4, 1081 Pyrrolopyrroles H NMR, 4, 1041 occurrence, 4, 1042 reactivity, 4, 1049 synthesis, 4, 1068 Pyrrolo[2,3-6]pyrroles ionization potentials, 4, 1046 synthesis, 4, 293, 1070 Pyrrolo[3,2-6]pyrroles synthesis, 6, 1009 Pyrrolo[3,2-6]pyrroles, dihydrosynthesis, 4, 1081 Pyrrolo[3,4-c]pyrroles applications, 4, 1083 Pyrroloquinolines... 

The Reisert compound 93, prepared from quinoline derivatives 92, gave upon reaction with dimethyl acetylenedicarboxylate the pyrroloquinoline 95. Reduction of 93 gave the tetrahydro derivative that upon reaction with dimethyl acetylenedicarboxylate afforded 96 (85JOC722). Reaction of 94 with acrylonitrile in presence of base gave pyrroloquinoline 97 (77JCS(P1)2018) (Scheme 18). 

Reaction of methyl 2-quinolylacetate with 2-A-trifluoroacetylamino-5-bromo-4-oxonorvaline methyl ester gave 103, a tryptophan analogue of pyrroloquinoline (96KG1510). 

Hydroxyethylation of 2,6-dimethylquinoline with ethylene oxide in presence of Li in PhBr gave 104 which was hydrogenated to the tetrahydro derivative 105. Its cyclization with P205/xylene gave the pyrroloquinoline 106. Nitration of 106 with fuming HNO3/H2SO4 afforded a mixture... 

Reaction of anthanilic acid 112 with acid anhydrides afforded the corresponding imide derivatives 113. Subjecting 113 to intramolecular Wittig cyclization has been achieved by treatment with A-phenyl(triphe-nylphosphoranylidene)etheneimine in toluene or dioxane whereby the corresponding pyrroloquinolines 116 were obtained (94TL9229). The intermediate 115 resulting from the rearrangement of 114 could be isolated when the reaction was done at room temperature (Scheme 22). 

CuCl/THF followed by catalytic hydrogenation to give the pyrroloquinoline 134. Nitration of the later gave the 9-nitro derivative 135. Reduction of 135 followed by reaction with ethyl trifluoroacetoacetate gave 136 that upon cyclization gave the tetracyclic compound 137 (98JMC623) (Scheme 26). 

Thermolysis of the azido derivative 143 (R = R =H) in refluxing 1,2-dichlorobenzene gave the pyrroloquinoline 144 and the dihydropyrrolo derivative 145 amongst other products (79H1021), whereas its thermal... 

Reaction of tetrahydroquinoline 257 with ethyl bromopyruvate afforded pyrroloquinoline 260 which upon transesterification by treatment with tropine in presence of sodium methoxide in toluene gave 261 which was found to be useful as 5-HT receptor antagonist (89EP322016). 

Regiospeciflc intramolecular cyclization of 3-carbomethoxyindole-l-propionic acid 273 with PPA took place on the 7-position to afford pyrroloquinoline 274 with no cyclization at the 2-posidon (86H2109) (Scheme 50). 

The aniline derivative 332, prepared from 2-fluoro-6-nitrotoluene, was transformed through successive reactions as shown in Scheme 60 to give the functionalized indole 333. It was then reduced with LiAlH4 to the dimethylaminopropyl derivative which was quaternized with Mel to the trimethyl ammonium salt 334. Subsequent cyclization and functionalization afforded the pyrroloquinoline 335. The latter could be transformed to the tetracyclic acid 336 (90JHC2151). (Scheme 60)... 

Magnusson, O.T. et al., Quinone biogenesis structure and mechanism of PqqC, the final catalyst in the production of pyrroloquinoline quinone, Proc. Natl. Acad. Sci. USA, 101, 7913, 2004. 

Conversion of methanol into formaldehyde by methanol dehydrogenase. A complex array of genes is involved in this oxidation and the dehydrogenase contains pyrroloquinoline quinone (PQQ) as a cofactor (references in Ramamoorthi and Lidstrom 1995). Details of its function must, however, differ from that of methylamine dehydrogenase that also contains a quinoprotein—tryptophan tryptophylquinone (TTQ). 

Ramamoorthi R, ME Lidstrom (1995) Transcriptional analysis of pqqD and study of the regulation of pyrroloquinoline quinone biosynthesis in Methylobacterium extorquens AMI. J Bacteriol Yll 206-211. 

Zayats M, Katz E, Baron R, Willner I. 2005. Reconstitution of apo-glucose dehydrogenase on pyrroloquinoline quinone-functionalized Au nanoparticles yields an electrically contacted hiocatalyst. J Am Chem Soc 127 12400-12406. 

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