A ¹³C study of hydroxymethyl derivatives of five‐membered ring heterocycles

Abstract

The I3C spectra of the hydroxymethyl derivatives of pyrrole, furan, 5,5-dimethylhydantoin, imidazole, thiophene, pyrazole, and phenol have been studied and assigned. The snbstitueot parameters for the hydroxymethyl group in pyrrole, thiophene, furan, and imidazole were determined.

Synthesis of azoles from 3-[(3-hydrazino-3-oxopropyl)anilino]-and 3-[(3-hydrazino-3-oxopropyl)-4-methylanilino]propane hydrazides

“…Formation of the pyrazole rings was confirmed by the presence of two methyl group singlets at 2.17 and 2.47 or 2.14 and 2.19 ppm and a methine singlet at 6.18 and 5.75 ppm in their 1 H NMR spectra. The carbon atom signals for the pyrazole rings were fully in agreement with analogous signals given for substituted pyrazoles [4][5][6]. Reaction of the dihydrazides 1 with phenyl isocyanate or phenyl isothiocyanate in methanol gave the hydrazinocarboxamide 3 and hydrazinocarbothioamide 4 derivatives, cyclization of which in basic medium gave 3-(2-{[2-(5-oxo-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]anilino}ethyl)-4-phenyl-4,5-dihydro-3H-1,2,4-triazol-5-one (5a) or its methyl derivative 5b and the thio analogs 6.…”

Aromatic compounds from the halotolerant fungal strain of Wallemia sebi PXP-89 in a hypersaline medium

“…1). Chemical study on secondary metabolites in 10% NaCl resulted in the isolation and identification of a new cyclopentanopyridine alkaloid, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta [b]pyridin-7-one (1), together with 11 aromatic compounds, (2S,3S)-1-(4-hydroxyphenyl) butane-2,3-diol (2) (Thornton and Jones, 1964), (2R,3S)-1-(4-hydroxyphenyl)butane-2,3-diol (3) (Thornton and Jones, 1964), (S)-3-hydroxy-4-(4-hydroxyphenyl)-2-one (4) (Yuki et al, 2009), 3-(hydroxyacetyl)indole (5) (Yang and Cordell, 1997), 1H-indole-3-carboxylic acid (6) (Burton et al, 1986), 5-hydroxy-3-coumaranone (7) (Lee et al, 2010), 4-methylfuran-2-carboxylic acid (8) (Sandham et al, 2004), 3-methylfuran (9) (Hiraoka, 1970), 5-methyluracil (10) (Ellis et al, 1973), 2,5-furandimethanol (11) (Katritzky and Law, 1988), and 5-methylpyridin-3-ol (12) (Boux et al, 1988). The absolute configurations of compounds 2-4 were determined for the first time.…”

Comparative Synthetic Strategies for the Generation of 5,10‐ and 5,15‐Substituted Push‐Pull Porphyrins

“…General Conditions: Details are as given in the Supporting Information (Section 1.1) or as reported earlier. [31b] All starting materials such as 2,5‐bis(hydroxymethyl)pyrrole ( 1 ), tripyrrane ( 2 ),[22b] 2,6‐dioctyloxybenzaldehyde,[8c] 3,5‐di‐ tert ‐butylbenzaldehyde, or 5,15‐disubstituted porphyrins[13b] were synthesized according to standard procedures.…”

“…5,10‐Bis(3,5‐di‐ tert ‐butylphenyl)porphyrin (7a): Porphyrin 7a was synthesized according to general procedure A. Tripyrrane (0.92 g, 4.12 mmol), 3,5‐di‐ tert ‐butylbenzaldehyde (1.80 g, 8.24 mmol), pyrrole (0.28 mL, 4.12 mmol), and TFA (0.20 mL, 0.63 equiv.) were dissolved in 1.50 L dry CH 2 Cl 2 .…”