Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups

Itaru Nakamura; Yusuke Sato; Sayaka Konta; Masahiro Terada

doi:10.1016/j.tetlet.2009.02.108

Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups

Itaru Nakamura, Yusuke Sato, Sayaka Konta, Masahiro Terada

Tohoku University

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

58 Citations (Scopus)

Abstract

The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI₄, affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.

Original language	English
Pages (from-to)	2075-2077
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.108
Publication status	Published - 2009 May 6

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10.1016/j.tetlet.2009.02.108

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title = "Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups",

abstract = "The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI4, affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.",

author = "Itaru Nakamura and Yusuke Sato and Sayaka Konta and Masahiro Terada",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research from Japan Society for Promotion in Science (JSPS) and The Uehara Memorial Foundation. We also thank reviewers for valuable suggestions. ",

year = "2009",

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T1 - Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups

AU - Nakamura, Itaru

AU - Sato, Yusuke

AU - Konta, Sayaka

AU - Terada, Masahiro

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research from Japan Society for Promotion in Science (JSPS) and The Uehara Memorial Foundation. We also thank reviewers for valuable suggestions.

PY - 2009/5/6

Y1 - 2009/5/6

N2 - The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI4, affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.

AB - The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI4, affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups

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