I-Catalyzed transformation of -aminobenzamide to -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...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 14; pp. 2678 - 2684
Main Authors Shamanth, Sadashivamurthy, Chaithra, Nagaraju, Gurukiran, Mahesha, Mamatha, Mahesha, Lokanath, N. K, Rangappa, Kanchugarakoppal S, Mantelingu, Kempegowda
Format Journal Article
LanguageEnglish
Published 08.04.2020
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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. 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.
Bibliography:1
For ESI and crystallographic data in CIF or other electronic format see DOI
H-NMR
13
C-NMR, and HRMS spectra of compounds and crystallographic data. CCDC
Electronic supplementary information (ESI) available: General experimental protocols, characterization details
1974299
10.1039/d0ob00118j
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00118j