A FACILE AND CONVENIENT SYNTHETIC METHOD FOR FLUORINE-CONTAINING DIBENZO[b,h][1,6]NAPHTHYRIDINES, THIOCHROMENO[3,2-c]QUINOLINES, AND CHROMENO[3,2-c]QUINOLINES

被引：9

作者：

Okada, Etsuji ^{[1
]}

Hatakenaka, Mizuki ^{[1
]}

Kuratani, Masayuki ^{[1
]}

Mori, Takashi ^{[1
]}

Ashida, Takuro ^{[1
]}

机构：

[1] Kobe Univ, Grad Sch Engn, Dept Chem Sci & Engn, Nada Ku, Kobe, Hyogo 6578501, Japan

来源：

HETEROCYCLES | 2014年 / 88卷 / 01期

关键词：

Dibenzonaphthyridine; Thiochromenoquinoline; Chromenoquinoline; Fluorine-Containing Heterocycle; Acid-Catalyzed Cyclization; CONTAINING HETEROCYCLIC-COMPOUNDS; NUCLEOPHILIC N-N; EXCHANGE-REACTION; SULFIDES; N,N-DIMETHYL-2,4-BISTRIFLUOROACETYL-1-NAPHTHYLAMINE;

D O I：

10.3987/COM-13-S(S)57

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel fluorine-containing dibenzo[b,h][1,6]naphthyridines (3), thiochromeno[3,2-c]quinolines (5), and chromeno[3,2-c]quinolines (7) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of N-aryl-3-trifluoroacetyl-4-quinolylamines (2) and aryl 3-trifluoroacetyl-4-quinolyl sulfides (4) and ethers (6), easily prepared by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1) with p-substituted anilines, thiophenols, and phenols, respectively.

引用

页码：799 / 806

页数：8

共 50 条

[31] Synthesis and pharmacological profile of 1-aryl-3-substituted pyrrolo[3,2-c]quinolines
Yum, EK
Kang, SK
Kim, SS
Choi, JK
Cheon, HG
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (19) : 2819 - 2822
[32] STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIMALARIAL INDOLO[3,2-C]QUINOLINES [1, 2]
WERBEL, LM
KESTEN, SJ
TURNER, WR
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (11) : 837 - 852
[33] SYNTHESES WITH NITRILES, L - CYCLIZATION TO PYRANO[3,2-C]PYRIDINES AND PYRANO[3,2-C]QUINOLINES WITH ETHOXYMETHYLENE-MALONITRILE AND ETHOXYMETHYLENEETHYL CYANOACETATE, RESP
SCHMIDT, HW
JUNEK, H
MONATSHEFTE FUR CHEMIE, 1978, 109 (05): : 1075 - 1080
[34] NEW SYNTHESIS OF BENZO[H]FURO[3,2-C]QUINOLINES, ISOSTERIC ANALOGS OF BENZO[C]PHENANTHRIDINES
DUVAL, O
GOMES, LM
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (01) : 153 - 159
[35] 1,4-CYCLOADDITION REACTIONS .3. SYNTHESIS OF FURO3,2-C!PYRIDO2,3-G!QUINOLINES, FURO2,3-A! 4,7!PHENANTHROLINES, FURO3,2-C!PYRROLO2,3-G!QUINOLINES, FURO3,2-C!PYRROLO3,2-G!QUINOLINES, AND FURO3,2-C!3-GQUINOLINES, FURO3,2-C!PYRROLO3,2-G!QUINOLINES, AND FURO3,2-C!EURO2',3' 4,5!PYRIDO2,3-G!QUINOLINES FROM 2,3-DIHYDRO-5-METHYLFURAN AND SCHIFF BASES
PERRICONE, SC
WORTH, DF
ELSLAGER, EF
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1970, 7 (03) : 537 - +
[36] A convenient preparation of thieno[3,2-c]pyrazole 1
Airey, John
Barrague, Matthieu
Edwards, Michael L.
Ferro, Michael
Friedrich, Dirk
Gillespy, Timothy A.
Jurcak, John
Musick, Kwon
Weintraub, Philip M.
Synthesis (Germany), 2014, 46 (01) : 96 - 100
[37] Construction of pyrrolo[3,2-c]quinolines -: Recent advances in the synthesis of the martinelline alkaloids
Nyerges, M
HETEROCYCLES, 2004, 63 (07) : 1685 - 1712
[38] Diastereoselective Synthesis of Novel and Enantiopure Tetrahy-dropyrano[3,2-c]quinolines
Moshapo, Paseka T.
Kinfe, Henok H.
SYNTHESIS-STUTTGART, 2015, 47 (23): : 3673 - 3686
[39] A facile and convenient synthetic method for fluorine-containing 1,2-dihydropyrido[3,2-h]quinazolines and pyrido[3,2-h]quinazolines
Okada, E
Tsukushi, N
HETEROCYCLES, 1999, 51 (10) : 2471 - 2478
[40] SYNTHESIS AND TRANSFORMATIONS OF SOME QUINOLINES AND 1H-PYRIDO[3,2-C]AZEPINES CONTAINING AMINO-ACID UNITS
ANZIC, B
KOCEVAR, M
POLANC, S
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (06) : 1305 - 1309

← 1 2 3 4 5 →