Sc(OTf)3-Catalyzed Iodocyclization/Ritter-Type Amidation of N-Alkoxypropiolamides: A Synthetic Strategy for Isoxazol-3(2H)-ones

被引：5

作者：

Yasui, Motohiro ^{[1
]}

Inoue, Maki ^{[1
]}

Nakao, Kotone ^{[1
]}

Takeda, Norihiko ^{[1
]}

Ueda, Masafumi ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 21期

关键词：

SUBSTITUTED ALPHA-CYANOACETATES; CATALYTIC ASYMMETRIC AMINATION; ELECTROPHILIC CYCLIZATION; OXIDATIVE CYCLIZATION; MEDIATED SYNTHESIS; FACILE SYNTHESIS; ACIDS; ANNULATION; CONSTRUCTION; HETEROCYCLES;

D O I：

10.1021/acs.joc.1c01987

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Sc(OTf)(3)-catalyzed iodocyclization/Ritter-type amidation of N-alkoxypropiolamides for the synthesis of 4-iodoisoxazol-3(2H)-ones bearing an amide group has been developed. This domino protocol allows the construction of a valuable heterocycle, isoxazol-3(2H)-one, as well as the introduction of two functional groups. The reaction has a broad substrate scope and can be carried out on a large scale. Control experiments suggest that Sc(OTf)(3) acts as a dual activator for both the iodocyclization and amidation steps. In addition, the N-alkoxy group in the substrate suppresses some of the side reactions.

引用

页码：15498 / 15508

页数：11

共 59 条

[1] Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes
Aggarwal, Trapti
Kumar, Sonu
Verma, Akhilesh K.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (32) : 7639 - 7653
[2] MOM-protected 3-hydroxy-5-phenyl-isoxazole: Regioselective preparation and synthetic application
Alzeer, J
Nock, N
Wassner, G
Masciadri, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (38) : 6857 - 6860
[3] Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles
Chen, Chin-Chau
Yang, Shyh-Chyun
Wu, Ming-Jung
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) : 10269 - 10274
[4] Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
China, Hideyasu
Kumar, Ravi
Kikushima, Kotaro
Dohi, Toshifumi
[J]. MOLECULES, 2020, 25 (24):
[5] Base-mediated reactions of N-alkyl-O-acyl hydroxamic acids:: synthesis of 3-oxo-2,3-dihydro-4-isoxazole carboxylic ester derivatives
Clark, AJ
Patel, D
Broadhurst, MJ
[J]. TETRAHEDRON LETTERS, 2003, 44 (42) : 7763 - 7765
[6] N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis
de Andrade, Vitor S. C.
de Mattos, Marcio C. S.
[J]. SYNTHESIS-STUTTGART, 2019, 51 (09): : 1841 - 1870
[7] Synthesis, anti-HIV activity, and metabolic stability of new alkenyldiarylmethane HIV-1 non-nucleoside reverse transcriptase inhibitors
Deng, BL
Hartman, TL
Buckheit, RW
Pannecouque, C
De Clercq, E
Fanwick, PE
Cushman, M
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (19) : 6140 - 6155
[8] Rh(I)-Catalyzed Decarbonylation of Diynones via C-C Activation: Orthogonal Synthesis of Conjugated Diynes
Dermenci, Alpay
Whittaker, Rachel E.
Dong, Guangbin
[J]. ORGANIC LETTERS, 2013, 15 (09) : 2242 - 2245
[9] SYNTHESIS AND SYNTHETIC UTILITY OF HALOLACTONES
DOWLE, MD
DAVIES, DI
[J]. CHEMICAL SOCIETY REVIEWS, 1979, 8 (02) : 171 - 197
[10] EVALUATION AND SYNTHESIS OF AMINOHYDROXYISOXAZOLES AND PYRAZOLES AS POTENTIAL GLYCINE AGONISTS
DRUMMOND, J
JOHNSON, G
NICKELL, DG
ORTWINE, DF
BRUNS, RF
WELBAUM, B
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) : 2116 - 2128

← 1 2 3 4 5 6 →