Homo- and Heteroannulation of sp3 C-H Bonds in Acetophenones for Divergent Synthesis of Thienothiazoles

被引：22

作者：

Pham, Phuc H. ^{[1
]}

Nguyen, Khang X. ^{[1
]}

Pham, Hoai T. B. ^{[1
,2
]}

Nguyen, Tung T. ^{[1
]}

Phan, Nam T. S. ^{[1
]}

机构：

[1] HCMC Univ Technol, VNU HCM, Fac Chem Engn, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam

[2] Univ Colorado, Dept Chem, Denver, CO 80204 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 21期

关键词：

CATALYZED ALPHA-ARYLATION; AROMATIC KETONES; CYCLIZATION; ALKENYLATION; CONDENSATION; POLYMERS; STRATEGY; PYRIDINE; OXIMES;

D O I：

10.1021/acs.orglett.9b03414

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of fused thieno[3,2-d]thiazoles via direct functionalization of C(sp(3))-H bonds in acetophenones was reported. The transformation is divergent to afford either 2-phenylbenzo[4,5]thieno[3,2-d]thiazoles or benzo[4,5]thieno[3,2-d]thiazol-2-yl(phenyl)methanones. Cross-coupling of acetophenones with C-H bonds in phenylacetic acids, methylazaarenes, and aldehydes was also feasible. Excellent tolerance of functionalities was observed. Our method marks a rare functionalization of C(sp(3))-H bonds in acetophenones to obtain heterocycles in the absence of prefunctionalized oxime esters.

引用

页码：8795 / 8799

页数：5

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