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

Akira Yoshimura; Michael T. Shea; Cody L. Makitalo; Melissa E. Jarvi; Gregory T. Rohde; Akio Saito; Mekhman S. Yusubov; Viktor V. Zhdankin

doi:10.3762/BJOC.14.87

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

Akira Yoshimura, Michael T. Shea, Cody L. Makitalo, Melissa E. Jarvi, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin

Chemistry & Biochemistry

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

9 Scopus citations

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 (US)
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
State	Published - May 8 2018

Bibliographical 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:
© 2018 Yoshimura et al.;

Keywords

Benziodazole
Biheterocycles
Hypervalent iodine
Iodine
Oxidatively assisted esterification

Access

10.3762/BJOC.14.87

OpenUrl availability

Full text

Cite this

@article{636ec701df974c19adcc5a7d28f35b81,

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.;",

year = "2018",

month = may,

day = "8",

doi = "10.3762/BJOC.14.87",

language = "English (US)",

volume = "14",

pages = "1016--1020",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Preparation, structure, and reactivity of bicyclic benziodazole

T2 - A new hypervalent iodine heterocycle

AU - Yoshimura, Akira

AU - Shea, Michael T.

AU - Makitalo, Cody L.

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.;

PY - 2018/5/8

Y1 - 2018/5/8

N2 - 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.

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.

KW - Benziodazole

KW - Biheterocycles

KW - Hypervalent iodine

KW - Iodine

KW - Oxidatively assisted esterification

UR - http://www.scopus.com/inward/record.url?scp=85053840824&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85053840824&partnerID=8YFLogxK

U2 - 10.3762/BJOC.14.87

DO - 10.3762/BJOC.14.87

M3 - Article

AN - SCOPUS:85053840824

SN - 1860-5397

VL - 14

SP - 1016

EP - 1020

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this