Expansion of diazepine heterocyclic chemical space: via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines

Anuradha Dagar; Ikyon Kim

doi:10.1039/d0ob02002h

Expansion of diazepine heterocyclic chemical space: via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines

Anuradha Dagar, Ikyon Kim

Department of Pharmacy

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

7 Citations (Scopus)

Abstract

A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.

Original language	English
Pages (from-to)	9836-9851
Number of pages	16
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	48
DOIs	https://doi.org/10.1039/d0ob02002h
Publication status	Published - 2020 Dec 28

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961, and NRF-2020R1I1A1A01074930) for generous financial support.

Publisher Copyright:
© The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Expansion of diazepine heterocyclic chemical space: via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines",

abstract = "A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.",

author = "Anuradha Dagar and Ikyon Kim",

note = "Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961, and NRF-2020R1I1A1A01074930) for generous financial support. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

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doi = "10.1039/d0ob02002h",

language = "English",

volume = "18",

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journal = "Organic and Biomolecular Chemistry",

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T1 - Expansion of diazepine heterocyclic chemical space

T2 - via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines

AU - Dagar, Anuradha

AU - Kim, Ikyon

N1 - Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961, and NRF-2020R1I1A1A01074930) for generous financial support. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/12/28

Y1 - 2020/12/28

N2 - A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.

AB - A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.

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SN - 1477-0520

VL - 18

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EP - 9851

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 48

ER -

Expansion of diazepine heterocyclic chemical space: via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines

Abstract

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