Synthesis of 1H-Isochromenes and 1,2-Dihydroisoquinolines by Indium(III)-Catalyzed Cycloisomerization of ortho -(Alkynyl)benzyl Derivatives

被引：8

作者：

Seoane-Carabel, Fabio

Alonso-Maranon, Lorena

Sarandeses, Luis A. ^{[1
]}

Sestelo, Jose Perez ^{[1
]}

机构：

[1] Univ A Coruna, CICA Ctr Interdisciplinar Quim & Biol, La Coruna 15071, Spain

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 11期

关键词：

homogeneous catalysis; indium catalysis; cycloisomerization; alkynes; pi-acid catalysis; CATALYZED INTRAMOLECULAR HYDROARYLATION; TRANSFER HYDROGENATION; CYCLIZATION; ISOCHROMENE; VERSATILE; ALKYNES; (Z)-1-ALKYLIDENE-1,3-DIHYDROISOBENZOFURANS; 2-ALKYNYLBENZALDEHYDE; ALKYNYLBENZALDEHYDES; 6-SULFONYLINDOLES;

D O I：

10.1055/s-0042-1751383

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1H-Isochromenes and 1,2-dihydroisoquinolines are synthe-sized by regioselective indium(III)-catalyzed intramolecular hydrofunctionalization of o-(alkynyl)benzyl derivatives. The reaction with o-(alkynyl)benzyl alcohols and amines proceeds using indium triiodide(5-10 mol%) in toluene at 80-100 degrees C via regioselective 6-endo-dig intra-molecular alkyne hydroalkoxylation or hydroamination in good yields.Alternatively, the cycloisomerization reaction of o-(alkynyl)benzalde-hydes and imine derivatives using InI3 (5 mol%) and the Hantzsch ester(120 mol%) takes place, under milder reaction conditions, to give a vari-ety of functionalized 1H-isochromenes and 1,2-dihydroisoquinolinesthrough a domino cycloisomerization/reduction approach.

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页码：1714 / 1723

页数：10

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