New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines

John Schwerkoske, Thierry Masquelin, Tom Perun, Christopher Hulme

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.

Original languageEnglish (US)
Pages (from-to)8355-8357
Number of pages3
JournalTetrahedron Letters
Volume46
Issue number48
DOIs
StatePublished - Nov 28 2005
Externally publishedYes

Fingerprint

Pyridines
Microwave irradiation
Microwaves
Aldehydes
Methanol
pyridine
scandium triflate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines. / Schwerkoske, John; Masquelin, Thierry; Perun, Tom; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 46, No. 48, 28.11.2005, p. 8355-8357.

Research output: Contribution to journalArticle

Schwerkoske, John ; Masquelin, Thierry ; Perun, Tom ; Hulme, Christopher. / New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 48. pp. 8355-8357.
@article{5751d9b638ca456cb63f9080bd6a2f6e,
title = "New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines",
abstract = "The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.",
author = "John Schwerkoske and Thierry Masquelin and Tom Perun and Christopher Hulme",
year = "2005",
month = "11",
day = "28",
doi = "10.1016/j.tetlet.2005.09.181",
language = "English (US)",
volume = "46",
pages = "8355--8357",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "48",

}

TY - JOUR

T1 - New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines

AU - Schwerkoske, John

AU - Masquelin, Thierry

AU - Perun, Tom

AU - Hulme, Christopher

PY - 2005/11/28

Y1 - 2005/11/28

N2 - The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.

AB - The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.

UR - http://www.scopus.com/inward/record.url?scp=27644469374&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27644469374&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.09.181

DO - 10.1016/j.tetlet.2005.09.181

M3 - Article

AN - SCOPUS:27644469374

VL - 46

SP - 8355

EP - 8357

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 48

ER -