Reaction of 1-methylpyrrole with 1,3-dichloro-5,5-disubstituted hydantoins: Products and AM1 study of intermediates

Michael De Rosa, Edward Melenski, Andrew J. Holder

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

The reaction of 1-methylpyrrole with 1,3-dichloro-5,5-dimethylhydantoin gave 3-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin and 1,3-di-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin as products. In contrast reaction with 1,3-dichloro-5-methyl-5-phenylhydantoin (3) or 1,3-dichloro-5,5-diphenylhydantoin (4) gave only the monopyrroylhydantoin derivatives. This difference was attributed to a steric interaction between the substituents on C-5 and N1.

Original languageEnglish (US)
Pages (from-to)1059-1064
Number of pages6
JournalHeterocycles
Volume36
Issue number5
DOIs
StatePublished - May 1 1993

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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