Iodine-mediated domino cyclization of hydrazides for one-pot synthesis of 1,3,4-oxadiazoles via oxidative bond cleavage of vinyl azide

Swadhapriya Bhukta; Rana Chatterjee; Kishore Kumar Angajala; Rambabu Dandela

doi:10.1016/j.tetlet.2023.154714

Iodine-mediated domino cyclization of hydrazides for one-pot synthesis of 1,3,4-oxadiazoles via oxidative bond cleavage of vinyl azide

Swadhapriya Bhukta, Rana Chatterjee, Kishore Kumar Angajala, Rambabu Dandela

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

4 Scopus citations

Abstract

An iodine and base-promoted domino cyclization has been disclosed for one-pot synthesis of 1,3,4-oxadiazoles via oxidative cleavage of C(sp2)-N and C(sp2)-C bonds. Herein, the use of potassium carbonate base was found to be crucial reagents in this oxidative cyclization and deacylation through selective bonds cleavage, affording mono and disubstituted 1,3,4-oxadiazoles respectively. The domino process provides a variety of substrate scope with moderate to good yields and is highly functional group compatible. Moreover, an important drug molecule fenadiazole was derived following the present procedure.

Original language	English
Article number	154714
Journal	Tetrahedron Letters
Volume	128
DOIs	https://doi.org/10.1016/j.tetlet.2023.154714
State	Published - 19 Sep 2023
Externally published	Yes

Keywords

1,3,4-oxadiazoles
Base promoted
Cleavage of C-N and C-C
Domino cyclization
Metal-free

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2023.154714

Cite this

@article{94f38b78018040b289b9c00f1087145f,

title = "Iodine-mediated domino cyclization of hydrazides for one-pot synthesis of 1,3,4-oxadiazoles via oxidative bond cleavage of vinyl azide",

abstract = "An iodine and base-promoted domino cyclization has been disclosed for one-pot synthesis of 1,3,4-oxadiazoles via oxidative cleavage of C(sp2)-N and C(sp2)-C bonds. Herein, the use of potassium carbonate base was found to be crucial reagents in this oxidative cyclization and deacylation through selective bonds cleavage, affording mono and disubstituted 1,3,4-oxadiazoles respectively. The domino process provides a variety of substrate scope with moderate to good yields and is highly functional group compatible. Moreover, an important drug molecule fenadiazole was derived following the present procedure.",

keywords = "1,3,4-oxadiazoles, Base promoted, Cleavage of C-N and C-C, Domino cyclization, Metal-free",

author = "Swadhapriya Bhukta and Rana Chatterjee and {Kumar Angajala}, Kishore and Rambabu Dandela",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = sep,

day = "19",

doi = "10.1016/j.tetlet.2023.154714",

language = "English",

volume = "128",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Iodine-mediated domino cyclization of hydrazides for one-pot synthesis of 1,3,4-oxadiazoles via oxidative bond cleavage of vinyl azide

AU - Bhukta, Swadhapriya

AU - Chatterjee, Rana

AU - Kumar Angajala, Kishore

AU - Dandela, Rambabu

PY - 2023/9/19

Y1 - 2023/9/19

N2 - An iodine and base-promoted domino cyclization has been disclosed for one-pot synthesis of 1,3,4-oxadiazoles via oxidative cleavage of C(sp2)-N and C(sp2)-C bonds. Herein, the use of potassium carbonate base was found to be crucial reagents in this oxidative cyclization and deacylation through selective bonds cleavage, affording mono and disubstituted 1,3,4-oxadiazoles respectively. The domino process provides a variety of substrate scope with moderate to good yields and is highly functional group compatible. Moreover, an important drug molecule fenadiazole was derived following the present procedure.

AB - An iodine and base-promoted domino cyclization has been disclosed for one-pot synthesis of 1,3,4-oxadiazoles via oxidative cleavage of C(sp2)-N and C(sp2)-C bonds. Herein, the use of potassium carbonate base was found to be crucial reagents in this oxidative cyclization and deacylation through selective bonds cleavage, affording mono and disubstituted 1,3,4-oxadiazoles respectively. The domino process provides a variety of substrate scope with moderate to good yields and is highly functional group compatible. Moreover, an important drug molecule fenadiazole was derived following the present procedure.

KW - 1,3,4-oxadiazoles

KW - Base promoted

KW - Cleavage of C-N and C-C

KW - Domino cyclization

KW - Metal-free

UR - http://www.scopus.com/inward/record.url?scp=85169547915&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2023.154714

DO - 10.1016/j.tetlet.2023.154714

M3 - Article

AN - SCOPUS:85169547915

SN - 0040-4039

VL - 128

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154714

ER -

Iodine-mediated domino cyclization of hydrazides for one-pot synthesis of 1,3,4-oxadiazoles via oxidative bond cleavage of vinyl azide

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this