AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols

Trinadh Kaicharla; Anu Jacob; Rajesh G. Gonnade; Akkattu T. Biju

doi:10.1039/c7cc03425c

AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols

Trinadh Kaicharla
, Anu Jacob
, Rajesh G. Gonnade
, Akkattu T. Biju

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

25 Scopus citations

Abstract

The reaction of 2-naphthols with aziridines in the presence of AgOTf resulting in a dehydrative, formal [3+2] annulation is reported. The reaction allows the synthesis of functionalized benzoindolines, and tolerates a broad range of functional groups. A preliminary study on the mechanism of this reaction indicates an S_N1-type ring-opening of aziridines. This method is demonstrated for the one-pot synthesis of benzoindoles.

Original language	English (US)
Pages (from-to)	8219-8222
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	58
DOIs	https://doi.org/10.1039/c7cc03425c
State	Published - 2017
Externally published	Yes

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© 2017 The Royal Society of Chemistry.

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title = "AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols",

abstract = "The reaction of 2-naphthols with aziridines in the presence of AgOTf resulting in a dehydrative, formal [3+2] annulation is reported. The reaction allows the synthesis of functionalized benzoindolines, and tolerates a broad range of functional groups. A preliminary study on the mechanism of this reaction indicates an SN1-type ring-opening of aziridines. This method is demonstrated for the one-pot synthesis of benzoindoles.",

author = "Trinadh Kaicharla and Anu Jacob and Gonnade, \{Rajesh G.\} and Biju, \{Akkattu T.\}",

note = "Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7cc03425c",

language = "English (US)",

volume = "53",

pages = "8219--8222",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols

AU - Kaicharla, Trinadh

AU - Jacob, Anu

AU - Gonnade, Rajesh G.

AU - Biju, Akkattu T.

PY - 2017

Y1 - 2017

N2 - The reaction of 2-naphthols with aziridines in the presence of AgOTf resulting in a dehydrative, formal [3+2] annulation is reported. The reaction allows the synthesis of functionalized benzoindolines, and tolerates a broad range of functional groups. A preliminary study on the mechanism of this reaction indicates an SN1-type ring-opening of aziridines. This method is demonstrated for the one-pot synthesis of benzoindoles.

AB - The reaction of 2-naphthols with aziridines in the presence of AgOTf resulting in a dehydrative, formal [3+2] annulation is reported. The reaction allows the synthesis of functionalized benzoindolines, and tolerates a broad range of functional groups. A preliminary study on the mechanism of this reaction indicates an SN1-type ring-opening of aziridines. This method is demonstrated for the one-pot synthesis of benzoindoles.

UR - https://www.scopus.com/pages/publications/85024853338

UR - https://www.scopus.com/pages/publications/85024853338#tab=citedBy

U2 - 10.1039/c7cc03425c

DO - 10.1039/c7cc03425c

M3 - Article

C2 - 28681868

AN - SCOPUS:85024853338

SN - 1359-7345

VL - 53

SP - 8219

EP - 8222

JO - Chemical Communications

JF - Chemical Communications

IS - 58

ER -

AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols

Abstract

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