A convenient procedure for the synthesis of fused fluoro isoquinolines

被引：12

作者：

Kiselyov, AS ^{[1
]}

机构：

[1] Chem Divers, Small Molecule Drug Discovery, San Diego, CA 92121 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 04期

关键词：

fluorine and compounds; condensations; quinone niethide; isoquinolines; anionically activated trifluoromethyl group;

D O I：

10.1016/j.tet.2005.10.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A base-promoted conversion of ortho-trifluoromethyl benzyl derivatives of NH-heterocycles into a respective fluorinated isoquinolines (38-57% isolated yields) is reported. The reaction is general for the benzylated derivatives of the electron-rich NH-heterocycles and the respective derivatives of pyrazole. The outcome of the reaction could be explained by an intermediate formation of a highly reactive quinone methide species. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：543 / 548

页数：6

共 17 条

[1] AN ACTIVATED TRIFLUOROMETHYL GROUP AS A NOVEL SYNTHON FOR A SUBSTITUTED VINYL FUNCTION - FACILE SYNTHESIS OF 2(SUBSTITUTED 1-ALKENYL)ANILINES [J].

HOJJAT, M ;

KISELYOV, AS ;

STREKOWSKI, L .

SYNTHETIC COMMUNICATIONS, 1994, 24 (02) :267-272

[2] SYNTHESIS OF FLUORO AND TRIFLUOROMETHYL DERIVATIVES OF 2-PHENYLQUINOLIN-4-OL [J].

JANDA, L ;

NGUYEN, J ;

PATTERSON, SE ;

STREKOWSKI, L .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (07) :1753-1756

[3] Synthesis of polysubstituted 4-fluoroquinolinones [J].

Kiselyov, AS ;

Piatnitski, EL ;

Doody, J .

ORGANIC LETTERS, 2004, 6 (22) :4061-4063

[4] The trifluoromethyl grow in organic synthesis. A review [J].

Kiselyov, AS ;

Strekowski, L .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (03) :289-&

[5] A novel synthesis of polysubstituted naphthalenes [J].

Kiselyov, AS .

TETRAHEDRON, 2001, 57 (25) :5321-5326

[6] AN UNCONVENTIONAL SYNTHETIC APPROACH TO FLUORO HETEROAROMATIC-COMPOUNDS BY A NOVEL TRANSFORMATION OF AN ANIONICALLY ACTIVATED TRIFLUOROMETHYL GROUP [J].

KISELYOV, AS ;

STREKOWSKI, L .

TETRAHEDRON LETTERS, 1994, 35 (41) :7597-7600

[7]

KISELYOV AS, 1994, HETEROCYCLES, V37, P775

[8] A facile one-pot synthesis of polysubstituted naphthalenes [J].

Kiselyov, AS .

TETRAHEDRON LETTERS, 2001, 42 (17) :3053-3056

[9] A novel and highly efficient synthesis of the aza analogs of tacrine [J].

Smith, L ;

Kiselyov, AS .

TETRAHEDRON LETTERS, 1999, 40 (31) :5643-5646

[10] A NOVEL ROUTE TO 7-(SUBSTITUTED AMINO)-5,6-DIHYDROBENZ[C]ACRIDINES [J].

STREKOWSKI, L ;

WYDRA, RL ;

HARDEN, DB ;

HONKAN, VA .

HETEROCYCLES, 1990, 31 (09) :1565-1569

← 1 2 →