Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones

Tao Zhang; Xunqing Dong; Hitesh B. Jalani; Jiaqi Zou; Guigen Li; Hongjian Lu

doi:10.1021/acs.orglett.9b01167

Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones

Tao Zhang, Xunqing Dong, Hitesh B. Jalani, Jiaqi Zou, Guigen Li, Hongjian Lu

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

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Abstract

A practical iridium-catalyzed cascade/stepwise synthesis of dihydroquinazolinones (DHQs) and bis-DHQs fused to medium to large N-heterocyclic rings is developed. The reaction undergoes benzamide-directed intermolecular C-H amination with an aldehyde-tethered alkyl azide, and then the newly installed amino group undergoes intramolecular cyclization with a remote aldehyde group present in azide and amidyl group of benzamide either intrinsically or catalyzed by phosphoric acid, facilitating the formation of bicyclic and/or tricyclic rings in a very efficient manner.

Original language	English
Pages (from-to)	3706-3710
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b01167
State	Published - May 17 2019

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title = "Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones",

abstract = "A practical iridium-catalyzed cascade/stepwise synthesis of dihydroquinazolinones (DHQs) and bis-DHQs fused to medium to large N-heterocyclic rings is developed. The reaction undergoes benzamide-directed intermolecular C-H amination with an aldehyde-tethered alkyl azide, and then the newly installed amino group undergoes intramolecular cyclization with a remote aldehyde group present in azide and amidyl group of benzamide either intrinsically or catalyzed by phosphoric acid, facilitating the formation of bicyclic and/or tricyclic rings in a very efficient manner.",

author = "Tao Zhang and Xunqing Dong and Jalani, {Hitesh B.} and Jiaqi Zou and Guigen Li and Hongjian Lu",

note = "Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21871131) and the Fundamental Research Funds for the Central Universities (020514380131). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b01167",

language = "English",

volume = "21",

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journal = "Organic Letters",

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T1 - Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones

AU - Zhang, Tao

AU - Dong, Xunqing

AU - Jalani, Hitesh B.

AU - Zou, Jiaqi

AU - Li, Guigen

AU - Lu, Hongjian

N1 - Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21871131) and the Fundamental Research Funds for the Central Universities (020514380131). Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/5/17

Y1 - 2019/5/17

N2 - A practical iridium-catalyzed cascade/stepwise synthesis of dihydroquinazolinones (DHQs) and bis-DHQs fused to medium to large N-heterocyclic rings is developed. The reaction undergoes benzamide-directed intermolecular C-H amination with an aldehyde-tethered alkyl azide, and then the newly installed amino group undergoes intramolecular cyclization with a remote aldehyde group present in azide and amidyl group of benzamide either intrinsically or catalyzed by phosphoric acid, facilitating the formation of bicyclic and/or tricyclic rings in a very efficient manner.

AB - A practical iridium-catalyzed cascade/stepwise synthesis of dihydroquinazolinones (DHQs) and bis-DHQs fused to medium to large N-heterocyclic rings is developed. The reaction undergoes benzamide-directed intermolecular C-H amination with an aldehyde-tethered alkyl azide, and then the newly installed amino group undergoes intramolecular cyclization with a remote aldehyde group present in azide and amidyl group of benzamide either intrinsically or catalyzed by phosphoric acid, facilitating the formation of bicyclic and/or tricyclic rings in a very efficient manner.

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Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones

Abstract

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