Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination

Shuklendu D. Karyakarte; Fatima C. Sequeira; Garrick H. Zibreg; Guoqing Huang; Josiah P. Matthew; Marina M.M. Ferreira; Sherry R. Chemler

doi:10.1016/j.tetlet.2015.01.171

Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination

Shuklendu D. Karyakarte
, Fatima C. Sequeira
, Garrick H. Zibreg
, Guoqing Huang
, Josiah P. Matthew
, Marina M.M. Ferreira
, Sherry R. Chemler

Chemistry

University at Buffalo

SUNY Buffalo

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

9 Scopus citations

Abstract

Abstract A new method for the synthesis of 2-aminomethyl functionalized 1,4-benzodiazepin-5-ones is presented. The benzodiazepine core is well-known to interact with biological receptors and many pharmaceutical drugs are derived from this structure. The alkene diamination strategy is employed for the first time for the synthesis of 1,4-benzodiazepinones. In this reaction, copper(2-ethylhexanoate)₂ serves as promoter and a range of external amines can be coupled with 2-sulfonamido-N-allyl benzamides to generate the 1,4-benzodiazepinones in good yields.

Original language	English
Article number	45841
Pages (from-to)	3686-3689
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.171
State	Published - Jul 3 2015

Keywords

1,4-Benzodiazepinones
Alkenes
Copper-promoted
Diamination

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10.1016/j.tetlet.2015.01.171

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title = "Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination",

abstract = "Abstract A new method for the synthesis of 2-aminomethyl functionalized 1,4-benzodiazepin-5-ones is presented. The benzodiazepine core is well-known to interact with biological receptors and many pharmaceutical drugs are derived from this structure. The alkene diamination strategy is employed for the first time for the synthesis of 1,4-benzodiazepinones. In this reaction, copper(2-ethylhexanoate)2 serves as promoter and a range of external amines can be coupled with 2-sulfonamido-N-allyl benzamides to generate the 1,4-benzodiazepinones in good yields.",

keywords = "1,4-Benzodiazepinones, Alkenes, Copper-promoted, Diamination",

author = "Karyakarte, \{Shuklendu D.\} and Sequeira, \{Fatima C.\} and Zibreg, \{Garrick H.\} and Guoqing Huang and Matthew, \{Josiah P.\} and Ferreira, \{Marina M.M.\} and Chemler, \{Sherry R.\}",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = jul,

day = "3",

doi = "10.1016/j.tetlet.2015.01.171",

language = "English",

volume = "56",

pages = "3686--3689",

journal = "Tetrahedron Letters",

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number = "23",

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TY - JOUR

T1 - Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination

AU - Karyakarte, Shuklendu D.

AU - Sequeira, Fatima C.

AU - Zibreg, Garrick H.

AU - Huang, Guoqing

AU - Matthew, Josiah P.

AU - Ferreira, Marina M.M.

AU - Chemler, Sherry R.

PY - 2015/7/3

Y1 - 2015/7/3

N2 - Abstract A new method for the synthesis of 2-aminomethyl functionalized 1,4-benzodiazepin-5-ones is presented. The benzodiazepine core is well-known to interact with biological receptors and many pharmaceutical drugs are derived from this structure. The alkene diamination strategy is employed for the first time for the synthesis of 1,4-benzodiazepinones. In this reaction, copper(2-ethylhexanoate)2 serves as promoter and a range of external amines can be coupled with 2-sulfonamido-N-allyl benzamides to generate the 1,4-benzodiazepinones in good yields.

AB - Abstract A new method for the synthesis of 2-aminomethyl functionalized 1,4-benzodiazepin-5-ones is presented. The benzodiazepine core is well-known to interact with biological receptors and many pharmaceutical drugs are derived from this structure. The alkene diamination strategy is employed for the first time for the synthesis of 1,4-benzodiazepinones. In this reaction, copper(2-ethylhexanoate)2 serves as promoter and a range of external amines can be coupled with 2-sulfonamido-N-allyl benzamides to generate the 1,4-benzodiazepinones in good yields.

KW - 1,4-Benzodiazepinones

KW - Alkenes

KW - Copper-promoted

KW - Diamination

UR - https://www.scopus.com/pages/publications/84939992830

U2 - 10.1016/j.tetlet.2015.01.171

DO - 10.1016/j.tetlet.2015.01.171

M3 - Article

SN - 0040-4039

VL - 56

SP - 3686

EP - 3689

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45841

ER -

Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination

Abstract

Keywords

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