A facile and rapid route for the synthesis of novel 1,5-substituted tetrazole hydantoins and thiohydantoins via a TMSN 3-Ugi/RNCX cyclization

Federico Medda, Christopher Hulme

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

This Letter describes novel methodology for the rapid assembly of new and biologically appealing 1,5-substituted tetrazole-hydantoins and thiohydantoins. The product of a TMSN 3-Ugi multi-component reaction is treated with an excess of isocyanate or isothiocyanate to generate the final scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

Original languageEnglish (US)
Pages (from-to)5593-5596
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number42
DOIs
StatePublished - Oct 17 2012

Fingerprint

Thiohydantoins
Hydantoins
Isocyanates
Cyclization
Scaffolds
1H-tetrazole
tetramethylsuccinonitrile
isothiocyanic acid

Keywords

  • Hydantoin
  • Multi-component reaction
  • Tetrazole
  • Trimethylsilylazide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{9d73b670606a477b84ab94687827ab22,
title = "A facile and rapid route for the synthesis of novel 1,5-substituted tetrazole hydantoins and thiohydantoins via a TMSN 3-Ugi/RNCX cyclization",
abstract = "This Letter describes novel methodology for the rapid assembly of new and biologically appealing 1,5-substituted tetrazole-hydantoins and thiohydantoins. The product of a TMSN 3-Ugi multi-component reaction is treated with an excess of isocyanate or isothiocyanate to generate the final scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.",
keywords = "Hydantoin, Multi-component reaction, Tetrazole, Trimethylsilylazide",
author = "Federico Medda and Christopher Hulme",
year = "2012",
month = "10",
day = "17",
doi = "10.1016/j.tetlet.2012.07.135",
language = "English (US)",
volume = "53",
pages = "5593--5596",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "42",

}

TY - JOUR

T1 - A facile and rapid route for the synthesis of novel 1,5-substituted tetrazole hydantoins and thiohydantoins via a TMSN 3-Ugi/RNCX cyclization

AU - Medda, Federico

AU - Hulme, Christopher

PY - 2012/10/17

Y1 - 2012/10/17

N2 - This Letter describes novel methodology for the rapid assembly of new and biologically appealing 1,5-substituted tetrazole-hydantoins and thiohydantoins. The product of a TMSN 3-Ugi multi-component reaction is treated with an excess of isocyanate or isothiocyanate to generate the final scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

AB - This Letter describes novel methodology for the rapid assembly of new and biologically appealing 1,5-substituted tetrazole-hydantoins and thiohydantoins. The product of a TMSN 3-Ugi multi-component reaction is treated with an excess of isocyanate or isothiocyanate to generate the final scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

KW - Hydantoin

KW - Multi-component reaction

KW - Tetrazole

KW - Trimethylsilylazide

UR - http://www.scopus.com/inward/record.url?scp=84866244616&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84866244616&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.07.135

DO - 10.1016/j.tetlet.2012.07.135

M3 - Article

AN - SCOPUS:84866244616

VL - 53

SP - 5593

EP - 5596

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 42

ER -