Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes

Rajeev Ranjan Jha; Abhinandan Kumar Danodia; Sushil Kumar; Akhilesh Kumar Verma

doi:10.1016/j.tetlet.2013.11.072

Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes

Rajeev Ranjan Jha, Abhinandan Kumar Danodia, Sushil Kumar, Akhilesh Kumar Verma

University of Delhi

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

13 Scopus citations

Abstract

An efficient tandem approach for the regio-and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies.

Original language	British English
Pages (from-to)	610-615
Number of pages	6
Journal	Tetrahedron Letters
Volume	55
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2013.11.072
State	Published - 15 Jan 2014

Keywords

Gold
Naphthyridines
Oxazole
Stereoselective
Tandem cyclization

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10.1016/j.tetlet.2013.11.072

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title = "Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes",

abstract = "An efficient tandem approach for the regio-and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies.",

keywords = "Gold, Naphthyridines, Oxazole, Stereoselective, Tandem cyclization",

author = "Jha, {Rajeev Ranjan} and Danodia, {Abhinandan Kumar} and Sushil Kumar and Verma, {Akhilesh Kumar}",

note = "Funding Information: We thank DU-DST PURSE Grant and DST for the financial assistance and USIC University of Delhi for the use of Instrumentation facility. R.R.J and A.D. is thankful to CSIR and RGNF for the Fellowship. ",

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doi = "10.1016/j.tetlet.2013.11.072",

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T1 - Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes

AU - Jha, Rajeev Ranjan

AU - Danodia, Abhinandan Kumar

AU - Kumar, Sushil

AU - Verma, Akhilesh Kumar

N1 - Funding Information: We thank DU-DST PURSE Grant and DST for the financial assistance and USIC University of Delhi for the use of Instrumentation facility. R.R.J and A.D. is thankful to CSIR and RGNF for the Fellowship.

PY - 2014/1/15

Y1 - 2014/1/15

N2 - An efficient tandem approach for the regio-and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies.

AB - An efficient tandem approach for the regio-and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies.

KW - Gold

KW - Naphthyridines

KW - Oxazole

KW - Stereoselective

KW - Tandem cyclization

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DO - 10.1016/j.tetlet.2013.11.072

M3 - Article

AN - SCOPUS:84891829199

SN - 0040-4039

VL - 55

SP - 610

EP - 615

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes

Abstract

Keywords

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