Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence

Athukuri Edukondalu; Sandip Sambhaji Vagh; Ting Han Lin; Wenwei Lin

doi:10.1039/d0cc08184a

Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence

Athukuri Edukondalu
, Sandip Sambhaji Vagh
, Ting Han Lin
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

6 Citations (Scopus)

Abstract

An efficient protocol for the chemoselective construction of the indeno[1,2-b]pyrroles and rearranged indeno[1,2-b]pyrrole derivatives is reportedviaanN-acylation/cyclization/Wittig reaction. Extensive mechanistic investigations revealed that the initially formed crucial spiro-indene-1,2′-[1,3,4]oxadiazol intermediate further reacts with phosphine to generate betaine, thus predominately resulting in the aforementioned heteroarenes proceeding by a Wittig reaction.

Original language	English
Pages (from-to)	2045-2048
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	16
DOIs	https://doi.org/10.1039/d0cc08184a
Publication status	Published - 2021 Feb 25

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d0cc08184a

Cite this

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title = "Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence",

abstract = "An efficient protocol for the chemoselective construction of the indeno[1,2-b]pyrroles and rearranged indeno[1,2-b]pyrrole derivatives is reportedviaanN-acylation/cyclization/Wittig reaction. Extensive mechanistic investigations revealed that the initially formed crucial spiro-indene-1,2′-[1,3,4]oxadiazol intermediate further reacts with phosphine to generate betaine, thus predominately resulting in the aforementioned heteroarenes proceeding by a Wittig reaction.",

author = "Athukuri Edukondalu and Vagh, \{Sandip Sambhaji\} and Lin, \{Ting Han\} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = feb,

day = "25",

doi = "10.1039/d0cc08184a",

language = "English",

volume = "57",

pages = "2045--2048",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence

AU - Edukondalu, Athukuri

AU - Vagh, Sandip Sambhaji

AU - Lin, Ting Han

AU - Lin, Wenwei

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/2/25

Y1 - 2021/2/25

N2 - An efficient protocol for the chemoselective construction of the indeno[1,2-b]pyrroles and rearranged indeno[1,2-b]pyrrole derivatives is reportedviaanN-acylation/cyclization/Wittig reaction. Extensive mechanistic investigations revealed that the initially formed crucial spiro-indene-1,2′-[1,3,4]oxadiazol intermediate further reacts with phosphine to generate betaine, thus predominately resulting in the aforementioned heteroarenes proceeding by a Wittig reaction.

AB - An efficient protocol for the chemoselective construction of the indeno[1,2-b]pyrroles and rearranged indeno[1,2-b]pyrrole derivatives is reportedviaanN-acylation/cyclization/Wittig reaction. Extensive mechanistic investigations revealed that the initially formed crucial spiro-indene-1,2′-[1,3,4]oxadiazol intermediate further reacts with phosphine to generate betaine, thus predominately resulting in the aforementioned heteroarenes proceeding by a Wittig reaction.

UR - https://www.scopus.com/pages/publications/85101530852

UR - https://www.scopus.com/pages/publications/85101530852#tab=citedBy

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DO - 10.1039/d0cc08184a

M3 - Article

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AN - SCOPUS:85101530852

SN - 1359-7345

VL - 57

SP - 2045

EP - 2048

JO - Chemical Communications

JF - Chemical Communications

IS - 16

ER -

Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence

Abstract

ASJC Scopus subject areas

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CCDC 2009731: Experimental Crystal Structure Determination

CCDC 2009644: Experimental Crystal Structure Determination

CCDC 2009643: Experimental Crystal Structure Determination

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Construction of indeno[1,2-b]pyrrolesviachemoselectiveN-acylation/cyclization/Wittig reaction sequence

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 2009731: Experimental Crystal Structure Determination

CCDC 2009644: Experimental Crystal Structure Determination

CCDC 2009643: Experimental Crystal Structure Determination

Cite this