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

Beilstein Journal of Organic Chemistry

卷:14

Cody L. Makitalo¹  Michael T. Shea¹  Melissa E. Jarvi¹  Akio Saito²  Gregory T. Rohde³  Akira Yoshimura⁴  Viktor V. Zhdankin⁴  Mekhman S. Yusubov⁴ 

[1] Department of Chemistry and Biochemistry, University of Minnesota, Duluth, MN 55812, USA;

[2] Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan;

[3] Marshall School, Duluth, MN 55811, USA,;

[4] The Tomsk Polytechnic University, 634050 Tomsk, Russia;

关键词: benziodazole;    biheterocycles;    hypervalent iodine;    iodine;    oxidatively assisted esterification;   

DOI  :  10.3762/bjoc.14.87

来源: DOAJ

【 摘 要 】

A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N’-diisopropylisophthalamide 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.

【 授权许可】

Unknown