PREPARATION OF PYRIDINE DERIVATIVES FROM THE CORRESPONDING 5-ACETAL-1-CARBONYL COMPOUNDS BY ACID PROMOTED CYCLIZATION

被引：0

作者：

Mihara, Hiromichi ^{[1
]}

Watanabe, Yuki ^{[1
]}

Konno, Hiroyuki ^{[1
]}

机构：

[1] Yamagata Univ, Dept Biol Engn, Grad Sch Sci & Engn, Yonezawa, Yamagata 9928510, Japan

来源：

HETEROCYCLES | 2021年 / 102卷 / 07期

基金：

日本学术振兴会;

关键词：

HIGHLY SUBSTITUTED PYRIDINES; CATALYZED CYCLIZATION; LIGANDS; OXIMES; ROUTE;

D O I：

10.3987/COM-21-14457

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of four alkylpyridine derivatives from 5-acetal-1-carbonyl compounds via the one-pot, acid-promoted cyclization of oxime intermediates is described. In addition, a dihydroxypyridine and pyridinium salt were also synthesized. The pyridine formation step was not affected by the stereochemistry of the precursors used.

引用

页码：1314 / 1329

页数：16

共 50 条

[31] INDOLE N-CARBONYL COMPOUNDS - PREPARATION AND COUPLING OF INDOLE-1-CARBOXYLIC ACID ANHYDRIDE
BOGER, DL
PATEL, M
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17): : 3934 - 3936
[32] ELECTROCHEMISTRY OF THE CYCLIZATION REACTION OF 1,1'-BINAPHTHYL DERIVATIVES .4. POLAROGRAPHIC-REDUCTION AND CYCLIZATION OF 1,1'-BINAPHTHYL-4,4',5,5'-TETRACARBOXYLIC ACID-DERIVATIVES
KHMELNITSKAYA, EY
ROMANOVA, KA
VOROZHTSOV, GN
ZHURNAL OBSHCHEI KHIMII, 1981, 51 (05): : 1187 - 1193
[33] Preparation of Spiro[indene-1,1'-isoindolin]-3'-ones via Sulfuric Acid-Promoted Cascade Cyclization
Sun, Lang
Liu, Peng
Wang, Jing
Lu, Ping
Wang, Yanguang
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (16): : 8407 - 8418
[34] Convenient one-pot synthesis of β-alkyl thio acid derivatives from thioacetates and the corresponding α,β-unsaturated compounds
Department of Chemistry, Sogang University, Seoul 121-742, Korea, Republic of
Synth. Commun., 11 (2189-2196):
[35] Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions
Barrero, AF
Alvarez-Manzaneda, EJ
Chahboun, R
TETRAHEDRON LETTERS, 2000, 41 (12) : 1959 - 1962
[36] Acid-Promoted [3+1+1] Cyclization of N-Tosylhydrazones and Isocyanides: A Method for the Preparation of 4,5-Diaminopyrazoles
Zhang, Qian
Tang, Meng
Zhang, Siyu
Wei, Zeyang
ORGANIC LETTERS, 2020, 22 (13) : 5182 - 5186
[37] Multicomponent condensation of 1,2-dihydropyrazol-3-one derivatives with carbonyl compounds and MeldrumA′s acid
Lichitskii, B. V.
Osipov, A. O.
Komogortsev, A. N.
Dudinov, A. A.
Krayushkin, M. M.
RUSSIAN CHEMICAL BULLETIN, 2015, 64 (05) : 1083 - 1088
[38] Multicomponent condensation of 1,2-dihydropyrazol-3-one derivatives with carbonyl compounds and Meldrum´s acid
B. V. Lichitskii
A. O. Osipov
A. N. Komogortsev
A. A. Dudinov
M. M. Krayushkin
Russian Chemical Bulletin, 2015, 64 : 1083 - 1088
[39] PREPARATION OF 4-HYDROXYSEMICARBAZIDE AND CYCLIZATION INTO 1,2,4-TRIAZOL-5-ONE DERIVATIVES .32. HYDROXYLAMINE DERIVATIVES
ZINNER, G
ARCHIV DER PHARMAZIE, 1968, 301 (11) : 827 - &
[40] ETHYLIDENETETRONIC ACID AND ITS DERIVATIVES - CONDENSATIONS WITH CARBONYL-COMPOUNDS, LEADING TO REASSIGNMENT OF RAMIGENIC ACID FROM PENICILLIUM-CHARLESII
BEGLEY, MJ
CLEMO, NG
PATTENDEN, G
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2393 - 2397

← 1 2 3 4 5 →