N-Heterocyclization of Naphthylamines with 1,2-and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System

被引：77

作者：

Aramoto, Hiroomi

Obora, Yasushi

Ishii, Yasutaka ^{[1
]}

机构：

[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 02期

关键词：

PRIMARY ALCOHOLS; KETONES; CYCLIZATION; QUINOLINES;

D O I：

10.1021/jo801966u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The N-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.

引用

页码：628 / 633

页数：6

共 50 条

[41] Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts
Amarasekara, Ananda S.
Animashaun, Moriam A.
CATALYSIS LETTERS, 2016, 146 (09) : 1819 - 1824
[42] Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts
Ananda S. Amarasekara
Moriam A. Animashaun
Catalysis Letters, 2016, 146 : 1819 - 1824
[43] RUTHENIUM COMPLEX-CATALYZED N-HETEROCYCLIZATION - SYNTHESES OF N-SUBSTITUTED PYRROLES AND PYRROLIDINES FROM 1,4-DIOLS AND PRIMARY AMINES
TSUJI, Y
YOKOYAMA, Y
HUH, KT
WATANABE, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) : 3456 - 3458
[44] CHEMISTRY OF ORGANIC FLUORINE-COMPOUNDS .29. PHOTOCHEMICAL CHLOROTRIFLUOROETHYLATION OF 1,2-DIOLS, 1,3-DIOLS AND 1,4-DIOLS
DEDEK, V
HEMER, I
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1985, 50 (12) : 2743 - 2752
[45] Regioselective synthesis of 1,2-and 1,3-diols from ω-hydroxy allyl acetates and carbonates via Pd complexes using boric acid and trialkyl borates
Cluzeau, J
Capdevielle, P
Cossy, J
TETRAHEDRON LETTERS, 2005, 46 (40) : 6945 - 6948
[46] Enantioselective synthesis of anti 1,3-diols via Ru(II)-catalyzed hydrogenations
Blanc, D
Ratovelomanana-Vidal, V
Marinetti, A
Genêt, JP
SYNLETT, 1999, (04) : 480 - 482
[47] A novel and efficient method for the catalytic direct oxidative carbonylation of 1,2-and 1,3-diols to 5-membered and 6-membered cyclic carbonates
Gabriele, Bartolo
Mancuso, Raffaella
Salerno, Giuseppe
Ruffolo, Giuseppe
Costa, Mirco
Dibenedetto, Angela
TETRAHEDRON LETTERS, 2009, 50 (52) : 7330 - 7332
[48] REDUCTION OF SYMMETRICAL 1,2- AND 1,3-DIKETONES WITH SODIUM BOROHYDRIDE, AND SEPARATION OF DIASTEREOISOMERIC 1,2- AND 1,3-DIOLS BY MEANS OF BORATE COMPLEXES
DALE, J
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAR): : 910 - &
[49] RUTHENIUM COMPLEX CATALYZED N-HETEROCYCLIZATION - SYNTHESES OF QUINOLINES AND INDOLE-DERIVATIVES FROM AMINOARENES AND 1,3-PROPANEDIOL OF GLYCOLS
TSUJI, Y
HUH, KT
WATANABE, Y
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09): : 1673 - 1680
[50] Novel Regiocontrolled Protection of 1,2- and 1,3-Diols via Mild Cleavage of Methylene Acetals
Fujioka, Hiromichi
Senami, Kento
Kubo, Ozora
Yahata, Kenzo
Minamitsuji, Yutaka
Maegawa, Tomohiro
ORGANIC LETTERS, 2009, 11 (22) : 5138 - 5141

← 1 2 3 4 5 →