An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles

John S. Schneekloth; Jr ,.Jimin Kim; Erik J. Sorensen

doi:10.1016/j.tet.2008.08.055

An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles

John S. Schneekloth
, Jr ,.Jimin Kim
, Erik J. Sorensen

Chemistry

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

58 Scopus citations

Abstract

In a variation of the classical Ugi reaction, an acid-promoted reaction between imines and isocyanides forms both 3-aminoindoles and substituted indoxyls. A recently reported triflyl phosphoramide is shown to be critical to obtain high yields under mild conditions.

Original language	English (US)
Pages (from-to)	3096-3101
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2008.08.055
State	Published - Apr 18 2009

All Science Journal Classification (ASJC) codes

Drug Discovery
Biochemistry
Organic Chemistry

Keywords

Heterocycles
Isocyanides
Multicomponent reactions
Synthetic methods

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10.1016/j.tet.2008.08.055

Cite this

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title = "An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles",

abstract = "In a variation of the classical Ugi reaction, an acid-promoted reaction between imines and isocyanides forms both 3-aminoindoles and substituted indoxyls. A recently reported triflyl phosphoramide is shown to be critical to obtain high yields under mild conditions.",

keywords = "Heterocycles, Isocyanides, Multicomponent reactions, Synthetic methods",

author = "Schneekloth, \{John S.\} and Kim, \{Jr ,.Jimin\} and Sorensen, \{Erik J.\}",

note = "Funding Information: This work was supported by the National Institute of General Medical Sciences (GM074763), Merck Research Laboratories, Boehringer Ingelheim, a Johnson \& Johnson Focused Giving Award, and Princeton University. J.S.S. thanks the NIH for a postdoctoral fellowship (F32GM078910). ",

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doi = "10.1016/j.tet.2008.08.055",

language = "English (US)",

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journal = "Tetrahedron",

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T1 - An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles

AU - Schneekloth, John S.

AU - Kim, Jr ,.Jimin

AU - Sorensen, Erik J.

N1 - Funding Information: This work was supported by the National Institute of General Medical Sciences (GM074763), Merck Research Laboratories, Boehringer Ingelheim, a Johnson & Johnson Focused Giving Award, and Princeton University. J.S.S. thanks the NIH for a postdoctoral fellowship (F32GM078910).

PY - 2009/4/18

Y1 - 2009/4/18

N2 - In a variation of the classical Ugi reaction, an acid-promoted reaction between imines and isocyanides forms both 3-aminoindoles and substituted indoxyls. A recently reported triflyl phosphoramide is shown to be critical to obtain high yields under mild conditions.

AB - In a variation of the classical Ugi reaction, an acid-promoted reaction between imines and isocyanides forms both 3-aminoindoles and substituted indoxyls. A recently reported triflyl phosphoramide is shown to be critical to obtain high yields under mild conditions.

KW - Heterocycles

KW - Isocyanides

KW - Multicomponent reactions

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/62049085173

UR - https://www.scopus.com/pages/publications/62049085173#tab=citedBy

U2 - 10.1016/j.tet.2008.08.055

DO - 10.1016/j.tet.2008.08.055

M3 - Article

C2 - 22163373

AN - SCOPUS:62049085173

SN - 0040-4020

VL - 65

SP - 3096

EP - 3101

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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