Preparation, structure, and reactivity of bicyclic benziodazole: A new hypervalent iodine heterocycle

Abstract

A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diiso-propylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.

Original language	English
Pages (from-to)	1016-1020
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/BJOC.14.87
Publication status	Published - 8 May 2018

Keywords

Benziodazole
Biheterocycles
Hypervalent iodine
Iodine
Oxidatively assisted esterification

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.3762/BJOC.14.87

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Preparation, structure, and reactivity of bicyclic benziodazole : A new hypervalent iodine heterocycle. / Yoshimura, Akira; Shea, Michael T.; Makitalo, Cody L.; Jarvi, Melissa E.; Rohde, Gregory T.; Saito, Akio; Yusubov, Mekhman S.; Zhdankin, Viktor V.

In: Beilstein Journal of Organic Chemistry, Vol. 14, 08.05.2018, p. 1016-1020.

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

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title = "Preparation, structure, and reactivity of bicyclic benziodazole: A new hypervalent iodine heterocycle",

abstract = "A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diiso-propylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.",

keywords = "Benziodazole, Biheterocycles, Hypervalent iodine, Iodine, Oxidatively assisted esterification",

author = "Akira Yoshimura and Shea, {Michael T.} and Makitalo, {Cody L.} and Jarvi, {Melissa E.} and Rohde, {Gregory T.} and Akio Saito and Yusubov, {Mekhman S.} and Zhdankin, {Viktor V.}",

note = "Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081). A.S. is also thankful to JSPS Grant-in-Aid for Scientific Research (C, Grant No 15K07852) and to the JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). V.V.Z. is thankful for support from the Office of the Vice President for Research, University of Minnesota. Publisher Copyright: {\textcopyright} 2018 Yoshimura et al.; Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2018",

month = may,

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doi = "10.3762/BJOC.14.87",

language = "English",

volume = "14",

pages = "1016--1020",

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AU - Yoshimura, Akira

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AU - Jarvi, Melissa E.

AU - Rohde, Gregory T.

AU - Saito, Akio

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor V.

N1 - Funding Information: This work was supported by a research grant from the Russian Science Foundation (RSF-16-13-10081). A.S. is also thankful to JSPS Grant-in-Aid for Scientific Research (C, Grant No 15K07852) and to the JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). V.V.Z. is thankful for support from the Office of the Vice President for Research, University of Minnesota. Publisher Copyright: © 2018 Yoshimura et al.; Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2018/5/8

Y1 - 2018/5/8

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AB - A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diiso-propylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.

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KW - Hypervalent iodine

KW - Iodine

KW - Oxidatively assisted esterification

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