Pyridoxal Model Compounds. I. The Regioselective Formylation of Methoxy-substituted Aromatic Compounds
スポンサーリンク
概要
- 論文の詳細を見る
9-Substituted 2-methoxyanthracenes (IVa–d) and -triptycenes (Va, b), and 3-substituted anisoles (VIa, b) were formylated by the use of the Vilsmeier-Haack method (Method A) and the metallation method using <I>n</I>-butyllithium (Method B). By the Method A, IVa–c, Vs', and VIs' were regioselectively formylated at C-1, C-3, and C-6 respectively, without exception, while by the Method B IVa–c, Va, VIa, and VIb were regioselectively formylated at C-3, C-3, C-2, and C-6 respectively, and Vb gave C-1 and C-3 formylated derivatives in the ratio of 10 to 1 respectively. Possible transition states concerning the occurrence of the regioselectivity were proposed and discussed.
- 公益社団法人 日本化学会の論文
著者
-
IWATA Masaaki
The Institute of Physical and Chemical Research
-
Emoto Sakae
The Institute of Physical and Chemical Research
関連論文
- Crystal Structures of N^2, N^5, N^8-Tri-p-toluenesulfonyl-2,5,8-triaza[9]-paracyclophane and N^2, N^5, N^8-Tri-p-toluenesulfonyl-14-hydroxy-15-hydroxymethyl-O^, O^′-isopropylidene-11-methyl-2,5,8-triaza[9](2,5)pyridinophane
- Crystal Structure of N, N'-Ditosyl-O, O'-dimesyl-3, 6-diazaoctane-1, 8-diol
- Crystal Structure of N^1, N^-Dibenzyl-N^5, N^, N^, N^-tetra(toluene-p-sulfonyl)-1, 5, 10, 14, 18, 23-hexaazacyclohexacosane : New 26-Membered Hexaaza-Coronand
- Catalytic activities of salicylaldehyde derivatives. V. Syntheses and catalytic activities of some trimethylammonio derivatives of salicylaldehyde in the racemization of L-glutamic acid.
- The use of Grignard reagents in the synthesis of carbohydrates. I. The synthesis of deoxy and branched-chain deoxy sugars.
- The use of Grignard reagents in the synthesis of carbohydrates. III. The one-way anomerization of methyl glycofuranosides and the opening of their furanose rings.
- Preferential introduction of a pyridylmethyl group into sulfonamides as an approach to an intramolular transimination.
- An improved oxidation method of pyridoxine.
- Catalytic Activities of Salicylaldehyde Derivatives. III. An Improved Synthesis of 6-Nitrosalicylaldehyde
- A simple regioselective partial hydrolysis of Di-O-isopropylidene monosaccharides with copper(II) ion.
- Pyridoxal model compounds. II. The Diels-Alder reaction of 9-substituted 2-methoxyanthracenes.
- Formation and Reduction of 2-Acyl-1-tetralones
- The Reaction of Several o-Methoxy Aromatic Aldehydes with Ethylthioxide. Novel Substitution and Condensation
- Catalytic activities of salicylaldehyde derivatives. VII. Synthesis and catalytic activity of (2-formyl-3-hydroxyphenyl)dimethylsulfonium salt in the racemization of L-glutamic acid.
- Aldol condensation of aldehydes with ketones promoted by the copper(II) ion. Orientation to the chemical model for metalloaldolases.
- Pyridoxal Model Compounds. I. The Regioselective Formylation of Methoxy-substituted Aromatic Compounds
- Asymmetric Synthesis with Sugar Derivatives. V. The Synthesis of α-Hydroxy Acids on Insoluble Polymer Supports