Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles

被引：17

作者：

Bissember, Alex C. ^{[1
]}

Banwell, Martin G. ^{[1
]}

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 13期

基金：

澳大利亚研究理事会;

关键词：

ANNULATED NICOTINE ANALOGS; ENANTIOSPECIFIC SYNTHESIS; GLUTAMIC ACID; ARYL HALIDES; EXCHANGE; DERIVATIVES; METAL;

D O I：

10.1021/jo9008386

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic. anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

引用

页码：4893 / 4895

页数：3

共 28 条

[1] ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD [J].

BARLUENGA, J ;

GONZALEZ, JM ;

GARCIAMARTIN, MA ;

CAMPOS, PJ ;

ASENSIO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2058-2060

[2] OPPI BRIEFS 4-IODO-6-METHOXYQUINOLINE [J].

Bissember, Alex C. ;

Banwell, Martin G. .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2008, 40 (06) :557-561

[3] PYRIDINE DERIVATIVES .2. SOME 6-METHYL-4-HYDROXY-2-PYRIDONES AND THEIR DERIVATIVES [J].

BRUCE, WF ;

PEREZMEDINA, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (11) :2571-2574

[4] NEW DERIVATIVES OF 3-METHYLISOXAZOLO[5,4-B]PYRIDINE [J].

CAMPARINI, A ;

PONTICELLI, F ;

TEDESCHI, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (03) :435-438

[5]

CLARK JH, 1987, CHEM COMMUN, P1409

[6] IODOPYRIDINES FROM BROMOPYRIDINES AND CHLOROPYRIDINES [J].

CORCORAN, RC ;

BANG, SH .

TETRAHEDRON LETTERS, 1990, 31 (47) :6757-6758

[7] The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands [J].

Fu, Gregory C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1555-1564

[8] Functionalized magnesium organometallics as versatile intermediates for the synthesis of polyfunctional heterocycles [J].

Ila, H ;

Baron, O ;

Wagner, AJ ;

Knochel, P .

CHEMICAL COMMUNICATIONS, 2006, (06) :583-593

[9] Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction [J].

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14844-14845

[10] 6-IODONICOTINIC ACID [J].

KLINGSBERG, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :1031-1031

← 1 2 3 →