Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

Sachin D. Gawande; Veerababurao Kavala; Manoj R. Zanwar; Chun Wei Kuo; Wen Chang Huang; Ting Shen Kuo; Hsiu Ni Huang; Chiu Hui He; Ching Fa Yao

doi:10.1002/adsc.201301020

Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

Sachin D. Gawande, Veerababurao Kavala, Manoj R. Zanwar, Chun Wei Kuo, Wen Chang Huang, Ting Shen Kuo, Hsiu Ni Huang, Chiu Hui He, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

23 Citations (Scopus)

Abstract

An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 0^2,7.0^9,14.0^16,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.

Original language	English
Pages (from-to)	2599-2608
Number of pages	10
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201301020
Publication status	Published - 2014 Aug 11

Keywords

C-N bond formation
Ullmann coupling
copper catalysts
dibenzodiazepinones
tandem processes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201301020

Cite this

@article{adbff673a84c45859c7fe0e96ce64e6a,

title = "Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation",

abstract = "An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 02,7.09,14.016,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.",

keywords = "C-N bond formation, Ullmann coupling, copper catalysts, dibenzodiazepinones, tandem processes",

author = "Gawande, {Sachin D.} and Veerababurao Kavala and Zanwar, {Manoj R.} and Kuo, {Chun Wei} and Huang, {Wen Chang} and Kuo, {Ting Shen} and Huang, {Hsiu Ni} and He, {Chiu Hui} and Yao, {Ching Fa}",

year = "2014",

month = aug,

day = "11",

doi = "10.1002/adsc.201301020",

language = "English",

volume = "356",

pages = "2599--2608",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11-12",

}

TY - JOUR

T1 - Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

AU - Gawande, Sachin D.

AU - Kavala, Veerababurao

AU - Zanwar, Manoj R.

AU - Kuo, Chun Wei

AU - Huang, Wen Chang

AU - Kuo, Ting Shen

AU - Huang, Hsiu Ni

AU - He, Chiu Hui

AU - Yao, Ching Fa

PY - 2014/8/11

Y1 - 2014/8/11

N2 - An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 02,7.09,14.016,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.

AB - An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 02,7.09,14.016,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.

KW - C-N bond formation

KW - Ullmann coupling

KW - copper catalysts

KW - dibenzodiazepinones

KW - tandem processes

UR - http://www.scopus.com/inward/record.url?scp=84906235331&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906235331&partnerID=8YFLogxK

U2 - 10.1002/adsc.201301020

DO - 10.1002/adsc.201301020

M3 - Article

AN - SCOPUS:84906235331

SN - 1615-4150

VL - 356

SP - 2599

EP - 2608

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 966266: Experimental Crystal Structure Determination

CCDC 966265: Experimental Crystal Structure Determination

CCDC 966267: Experimental Crystal Structure Determination

Cite this

Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 966266: Experimental Crystal Structure Determination

CCDC 966265: Experimental Crystal Structure Determination

CCDC 966267: Experimental Crystal Structure Determination

Cite this