On the reactivity of nitrosoimidazoles with acids (the Cusmano-Ruccia reaction): a continuous source of new ring- into-ring interconversion

Vincenzo Frenna, Mirella Rambaldi, Barbara Cosimelli, Domenico Spinelli, Elda Severi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

An extension of the ‘Cusmano–Ruccia’ reaction is reported. 6-(4-chlorophenyl)-3-methyl-5-nitrosoimi-dazo[2,1-b]oxazole by the action of hydrochloric acid gives 3-(4-chlorobenzoyl)-5-methyl-1,2,4-oxadiaz-ole (13); presumably via ammonium ion, CO2 and methanol elimination. The relevance of the nature of the atom of the B-ring linked to C-2 of the imidazole for the occurrence of the ring-into-ring interconver-sion has been once more confirmed.
Original languageEnglish
Pages (from-to)1488-1490
Number of pages3
JournalTetrahedron Letters
Volume55
Publication statusPublished - 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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