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

doi:10.1016/j.tetlet.2012.07.135

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 journal › Article › peer-review

22 Scopus citations

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 language	English (US)
Pages (from-to)	5593-5596
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.135
State	Published - Oct 17 2012

Keywords

Hydantoin
Multi-component reaction
Tetrazole
Trimethylsilylazide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.07.135

Cite this

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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",

note = "Funding Information: This research was supported by the NIH ( RC2MH090878 and P41GM086190 ). We acknowledge Dr. Sue A. Roberts and Mr. Gabriel H. Hall for small molecule X-ray crystal structure determination, and are grateful to Dr. David Bishop for proofreading and editing the final version of the text and graphics. ",

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AU - Medda, Federico

AU - Hulme, Christopher

N1 - Funding Information: This research was supported by the NIH ( RC2MH090878 and P41GM086190 ). We acknowledge Dr. Sue A. Roberts and Mr. Gabriel H. Hall for small molecule X-ray crystal structure determination, and are grateful to Dr. David Bishop for proofreading and editing the final version of the text and graphics.

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

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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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

Keywords

ASJC Scopus subject areas

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CCDC 922820: Experimental Crystal Structure Determination

Cite this

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

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 922820: Experimental Crystal Structure Determination

Cite this

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