Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization
with 2,2,2-Trichloroethoxycarbonyl Azide

Tao Zhang; Zhen Wang; Xuejiao Hu; Meng Yu; Tianning Deng; Guigen Li; Hongjian Lu

Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization with 2,2,2-Trichloroethoxycarbonyl Azide

Tao Zhang, Zhen Wang, Xuejiao Hu, Meng Yu, Tianning Deng, Guigen Li, Hongjian Lu

Chemistry and Biochemistry

Research output: Contribution to journal › Article

Abstract

An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.

Original language	English
Pages (from-to)	4898-4905
Journal	Journal of Organic Chemistry
State	Published - Jun 2016

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@article{9131cdf6f96b4e0c81a815619b236a85,

title = "Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization with 2,2,2-Trichloroethoxycarbonyl Azide",

abstract = "An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.",

author = "Tao Zhang and Zhen Wang and Xuejiao Hu and Meng Yu and Tianning Deng and Guigen Li and Hongjian Lu",

year = "2016",

month = jun,

language = "English",

pages = "4898--4905",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

}

TY - JOUR

T1 - Cesium Carboxylate-Promoted Iridium Catalyzed C-H Amidation/Cyclization with 2,2,2-Trichloroethoxycarbonyl Azide

AU - Zhang, Tao

AU - Wang, Zhen

AU - Hu, Xuejiao

AU - Yu, Meng

AU - Deng, Tianning

AU - Li, Guigen

AU - Lu, Hongjian

PY - 2016/6

Y1 - 2016/6

N2 - An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.

AB - An Ir(III)-catalyzed direct C-H amidation/cyclization of benzamides using 2,2,2-trichloroethoxycarbonyl azide (TrocN3) as the aminocarbonyl source is reported. With the aid of cesium carboxylate, the reactions proceed efficiently and with high regioselectivity, producing various functionalized quinazoline-2,4(1H,3H)-diones, which are important building blocks and key synthetic intermediates for biologically and medicinally important compounds. During the reactions, two new C-N bonds were formed by breaking C-H and N-H bonds sequence.

M3 - Article

SP - 4898

EP - 4905

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -