Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Arthur Y. Shaw, Zhigang Xu, Christopher Hulme

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

Original languageEnglish (US)
Pages (from-to)1998-2000
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number15
DOIs
StatePublished - Apr 11 2012

Fingerprint

Oxazoles
Carboxylic Acids
Ammonia
Scaffolds
Acids

Keywords

  • 2,4,5-Trisubstituted oxazoles
  • Multicomponent reactions
  • Robinson-Gabriel reaction
  • Ugi reaction
  • Vilsmeier-Haack reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles. / Shaw, Arthur Y.; Xu, Zhigang; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 53, No. 15, 11.04.2012, p. 1998-2000.

Research output: Contribution to journalArticle

@article{954f69efdfe14a8ca00d4fcb81aec686,
title = "Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles",
abstract = "This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.",
keywords = "2,4,5-Trisubstituted oxazoles, Multicomponent reactions, Robinson-Gabriel reaction, Ugi reaction, Vilsmeier-Haack reaction",
author = "Shaw, {Arthur Y.} and Zhigang Xu and Christopher Hulme",
year = "2012",
month = "4",
day = "11",
doi = "10.1016/j.tetlet.2012.02.030",
language = "English (US)",
volume = "53",
pages = "1998--2000",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "15",

}

TY - JOUR

T1 - Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

AU - Shaw, Arthur Y.

AU - Xu, Zhigang

AU - Hulme, Christopher

PY - 2012/4/11

Y1 - 2012/4/11

N2 - This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

AB - This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

KW - 2,4,5-Trisubstituted oxazoles

KW - Multicomponent reactions

KW - Robinson-Gabriel reaction

KW - Ugi reaction

KW - Vilsmeier-Haack reaction

UR - http://www.scopus.com/inward/record.url?scp=84862776950&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862776950&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.02.030

DO - 10.1016/j.tetlet.2012.02.030

M3 - Article

AN - SCOPUS:84862776950

VL - 53

SP - 1998

EP - 2000

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 15

ER -