2-hydroxymethyl-3-hydroxy

Chemical Name 2-Hydroxymethyl-3-hydroxy-(1-hydroxy-2-tert-butylaminoethyl)pyridine Common Name —... 

Naturally occurring and synthetic polyhydroxylated pyrrolidine and piperidines have recently received considerable attention due to their biological activities. Barco has used tandem Michael-Henry reactions to synthesize 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidines, from which the nitro group is removed to give the natural product, trans 2-hydroxymethyl-3-hy-droxypyrrolidine (Eq. 7.72).91... 

Compound 3 and 4 are mixture of epimers. The UV, IR, NMR (including 2D NMR) and MS spectra suggested that 3 and 4 are benzyl-dioxyhexane lignan (6,13) 3-[3-(3,4,5-trimethoxyphenyl)-2,3-dihydro-2-hydroxymethyl-hydroxy-... 

The reaction conditions can be varied so that only one of those monomers is formed. 1-Hydroxy-methylurea and l,3-bis(hydroxymethyl)urea condense in the presence of an acid catalyst to produce urea formaldehyde resins. A wide variety of resins can be obtained by careful selection of the pH, reaction temperature, reactant ratio, amino monomer, and degree of polymerization. If the reaction is carried far enough, an infusible polymer network is produced. 

In E. coli GTP cyclohydrolase catalyzes the conversion of GTP (33) into 7,8-dihydroneoptetin triphosphate (34) via a three-step sequence. Hydrolysis of the triphosphate group of (34) is achieved by a nonspecific pyrophosphatase to afford dihydroneopterin (35) (65). The free alcohol (36) is obtained by the removal of residual phosphate by an unknown phosphomonoesterase. The dihydroneoptetin undergoes a retro-aldol reaction with the elimination of a hydroxy acetaldehyde moiety. Addition of a pyrophosphate group affords hydroxymethyl-7,8-dihydroptetin pyrophosphate (37). Dihydropteroate synthase catalyzes the condensation of hydroxymethyl-7,8-dihydropteroate pyrophosphate with PABA to furnish 7,8-dihydropteroate (38). Finally, L-glutamic acid is condensed with 7,8-dihydropteroate in the presence of dihydrofolate synthetase. 

Pyrrole has been condensed under alkaline conditions with formaldehyde to give products of either N- or C-hydroxymethylation (Scheme 22). Although acid-catalyzed hydroxy-methylation is not a practical possibility, by addition of a reducing agent to the reaction mixture overall reductive alkylation can be achieved (Scheme 23). 

In many cases, substituents linked to a pyrrole, furan or thiophene ring show similar reactivity to those linked to a benzenoid nucleus. This generalization is not true for amino or hydroxyl groups. Hydroxy compounds exist largely, or entirely, in an alternative nonaromatic tautomeric form. Derivatives of this type show little resemblance in their reactions to anilines or phenols. Thienyl- and especially pyrryl- and furyl-methyl halides show enhanced reactivity compared with benzyl halides because the halogen is made more labile by electron release of the type shown below. Hydroxymethyl and aminomethyl groups on heteroaromatic nuclei are activated to nucleophilic attack by a similar effect. 

Carbazole, 2-hydroxy-reactions with citral, 4, 235 Carbazole, 2-hydroxy-9-methyl-synthesis, 4, 294 Carbazole, N-hydroxymethyl-as metabolite of carbazole, 1, 230 Carbazole, N-isopropyl-PE spectroscopy, 4, 190 Carbazole, A7-methyl- N NMR, 4, 175 X-ray spectroscopy, 4, 163 Carbazole, 1-nitro-synthesis, 4, 282 Carbazole, tetrahydro-dehydrogenation, 4, 282, 312 synthesis, 4, 107, 337, 353 Carbazole, 1,2,3,4-tetrahydro-reduction, 4, 255, 256 synthesis, 4, 312, 325, 352 Carbazole, 1,2,3,4-tetrahydro-1 -oxo-synthesis, 4, 337 Carbazole, 9-trifluoroacetyl-synthesis, 4, 218 Carbazole, vinyl-polymers, 1, 275, 301 Carbazole, 9-vinyl-copolymer... 

Chromanone, 3-acetamido-2-methyl-reduction, 3, 729 Chromanone, 3-amino-synthesis, 3, 734 Chromanone, 3-arylidene-thermoisomerization, 3, 722 Chromanone, 3-benzylidene-thermolysis, 3, 728 Chromanone, 3-bromo-2-hydroxy-benzofuran from, 3, 729 Chromanone, 6,8-dimethyl-hydroxymethylation, 3, 731 Chromanone, 2,3-epoxy-as synthon, 3, 735... 

Imidazole, 5-hydroxy-1 -isopropyl-2-methyl-4-propyl-synthesis, S, 475 Imidazole, 2-hydroxymethyl-hydroxymethylation, S, 404 oxidation, S, 430 Imidazole, 4-hydroxymethyl-oxidation, S, 430 synthesis, S, 480, 484 Imidazole, 2-hydroxymethyl-4-methyl-synthesis, S, 484... 

Indole, 3-hydroxymethyl-2-phenyl-stability, 4, 272 Indole, I-hydroxy-2-phenyl-synthesis, 4, 363 Indole, 2-iodo-synthesis, 4, 216 Indole, 3-iodo-reaetions, 4, 307 synthesis, 4, 216 Indole, 2-iodo-l-methyl-reaetions, 4, 307 Indole, 2-lithio-synthesis, 4, 308 Indole, 3-lithio-synthesis, 4, 308 Indole, 2-mereapto-tautomerism, 4, 38, 199 Indole, 3-mercapto-tautomerism, 4, 38, 199 Indole, 3-methoxy-synthesis, 4, 367 Indole, 5-methoxy-oxidation, 4, 248 Indole, 7-methoxy-2,3-dimethyl-aeetylation, 4, 219 benzoylation, 4, 219 Indole, 5-methoxy-l-methyl-reduetion, 4, 256 Indole, 5-methoxy-l-methyl-3-(2-dimethylaminoethyl)-reaetions... 

Indolizine, hydroxy-conformations, 4, 451 GLC retention times, 4, 451 synthesis, 4, 121 tautomerism, 4, 198, 452 Indolizine, 2-hydroxy-synthesis, 4, 463 Indolizine, 8-hydroxy-conformation, 4, 452 Indolizine, 2-hydroxymethyl-synthesis, 4, 461 Indolizine, 3-hydroxymethyl-synthesis, 4, 461 Indolizine, 6-hydroxymethyl-synthesis, 4, 461 Indolizine, methyl-mass spectra, 4, 187, 450 NM 4, 448 Indolizine, 2-methyl-diazo coupling, 4, 454 mass spectra, 2, 529, 4, 450 nitration, 4, 50, 454 nitrosation, 4, 454 reaction with diaryl disulfide, 4, 460 reaction with nitroethane, 4, 460 Indolizine, 3-methyl-basicity, 4, 454 Indolizine, 5-methyl-acidity, 4, 461 synthesis, 4, 466 Indolizine, 6-methyl-mass spectra, 4, 450 Indolizine, l-methyl-2-phenyl-nitration, 4, 454 nitrosation, 4, 454, 455 Indolizine, 3-methyl-2-phenyl-reaction... 

Kojic acid — see also Pyran-4-one, 5-hydroxy-2-hydroxymethyl-, 3, 611 acylation, 3, 697 application, 3, 880 occurrence, 3, 692 reactions, 3, 714, 715 with amines, 3, 700 with phenylhydrazine, 3, 700 synthesis, 3, 810 Kokusagine occurrence, 4, 989 Kokusaginine occurrence, 4, 989 synthesis, 4, 990 Koopmans theorem, 2, 135 Kostanecki-Robinson reaction chromone and coumarin formation in, 3, 819-821 mechanism, 3, 820 flavones, 3, 819... 

Pteridine, 4-hydroxy-3,4-dihydro-reactions, 3, 265 Pteridine, 6-hydroxymethyl-synthesis, 3, 311... 

Pyran-4-one, 3-ethoxy-2-methyl-, 3, 612 IR spectra, 3, 595 Pyran-4-one, 2-hydroxy-tautomerism, 3, 642 Pyran-4-one, 3-hydroxy-appiication, 3, 880 synthesis, 2, 91 3, 815 Pyran-4-one, 5-hydroxy-2-hydroxymethyl- C NMR, 3, 588 mass spectra, 3, 611... 

Pyrazolidine, l,2-diethyl-3-hydroxymethyl-biological activity, 5, 297 Pyrazolidine, 2-ethoxycarbonyl-l-phenyl-reactions, 5, 257 Pyrazolidine, 4-hydroxy-synthesis, 5, 155 Pyrazolidine, 1-phenyl-... 

Pyrrole, 3-hydroxy-geometry, 4, 158 synthesis, 4, 343 tautomerism, 4, 36, 198 Pyrrole, 3-([Pg.816]

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