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

doi:10.3987/COM-92-6274

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

Penn State Brandywine

Research output: Contribution to journal › Article › peer-review

4 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 language	English (US)
Pages (from-to)	1059-1064
Number of pages	6
Journal	Heterocycles
Volume	36
Issue number	5
DOIs	https://doi.org/10.3987/COM-92-6274
State	Published - May 1 1993

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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

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.",

author = "\{De Rosa\}, Michael and Edward Melenski and Holder, \{Andrew J.\}",

year = "1993",

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doi = "10.3987/COM-92-6274",

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T1 - Reaction of 1-methylpyrrole with 1,3-dichloro-5,5-disubstituted hydantoins

T2 - Products and AM1 study of intermediates

AU - De Rosa, Michael

AU - Melenski, Edward

AU - Holder, Andrew J.

PY - 1993/5/1

Y1 - 1993/5/1

N2 - 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.

AB - 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.

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

Abstract

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