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

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 wi...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 14; pp. 2678 - 2684
Main Authors Sadashivamurthy Shamanth, Nagaraju Chaithra, Gurukiran, Mahesha, Mahesha Mamatha, Lokanath, N K, Rangappa, Kanchugarakoppal S, Kempegowda Mantelingu
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 14.04.2020
Subjects
Chemical synthesis
Crystallography
Iodine
NMR
Nuclear magnetic resonance
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Summary: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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00118j