I2-Catalyzed transformation of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates

Sadashivamurthy Shamanth; Nagaraju Chaithra; Mahesha Gurukiran; Mahesha Mamatha; N. K. Lokanath; Kanchugarakoppal S. Rangappa; Kempegowda Mantelingu

doi:10.1039/D0OB00118J

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I₂-Catalyzed transformation of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates†

Sadashivamurthy Shamanth,^a Nagaraju Chaithra,^a Mahesha Gurukiran,^a Mahesha Mamatha,^b N. K. Lokanath,^c Kanchugarakoppal S. Rangappa*^a and Kempegowda Mantelingu

*^a

Author affiliations

* Corresponding authors

^a DOS in Chemistry, Manasagangotri, University of Mysore, Mysuru-570006, Karnataka, India
E-mail: kmlingu@gmail.com, rangappaks@gmail.com

^b SRSMNGFG College, Barkur-576210, Udupi Dist., Karnataka, India

^c DOS in Physics, Manasagangotri, University of Mysore, Mysuru-570006, India

Abstract

The present work describes an unexpected and unique protocol for the iodine catalysed synthesis of o-ureidobenzonitriles using o-aminobenzamides and isothiocyanates via intramolecular rearrangement. The metal-free route achieved here is insensitive to moisture and applicable to the synthesis of a wide variety of o-ureidobenzonitriles with excellent yields even in a scalable fashion.

This article is part of the themed collection: Supramolecular chemistry in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB00118J
Article type: Paper
Submitted: 18 Jan 2020
Accepted: 16 Mar 2020
First published: 17 Mar 2020

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Org. Biomol. Chem., 2020,18, 2678-2684

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I₂-Catalyzed transformation of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates

S. Shamanth, N. Chaithra, M. Gurukiran, M. Mamatha, N. K. Lokanath, K. S. Rangappa and K. Mantelingu, Org. Biomol. Chem., 2020, 18, 2678 DOI: 10.1039/D0OB00118J

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Organic & Biomolecular Chemistry