A convenient method for the synthesis of N-hydroxyureas

Dennis A Parrish; Zhou Zou; C Leigh Allen; Cynthia S. Day; S Bruce King

A convenient method for the synthesis of N-hydroxyureas

Dennis A Parrish, Zhou Zou, C Leigh Allen, Cynthia S. Day, S Bruce King

Medicinal Chemistry

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

23 Scopus citations

Abstract

Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In addition to primary and secondary aliphatic and aromatic amines, this method converts amino sugars to the corresponding N-hydroxyureas without extensive protecting group chemistry.

Original language	English (US)
Pages (from-to)	8841-8843
Journal	Tetrahedron Letters
State	Published - Nov 7 2005

Keywords

N-Hydroxyureas
nitric oxide
nitric oxide donors
Carbohydrates
Hydrogenation

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http://www.sciencedirect.com/science/article/pii/S0040403905023245

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title = "A convenient method for the synthesis of N-hydroxyureas",

abstract = "Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In addition to primary and secondary aliphatic and aromatic amines, this method converts amino sugars to the corresponding N-hydroxyureas without extensive protecting group chemistry.",

keywords = "N-Hydroxyureas, nitric oxide, nitric oxide donors, Carbohydrates, Hydrogenation",

author = "Parrish, {Dennis A} and Zhou Zou and Allen, {C Leigh} and Day, {Cynthia S.} and King, {S Bruce}",

year = "2005",

month = nov,

day = "7",

language = "English (US)",

pages = "8841--8843",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - A convenient method for the synthesis of N-hydroxyureas

AU - Parrish, Dennis A

AU - Zou, Zhou

AU - Allen, C Leigh

AU - Day, Cynthia S.

AU - King, S Bruce

PY - 2005/11/7

Y1 - 2005/11/7

N2 - Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In addition to primary and secondary aliphatic and aromatic amines, this method converts amino sugars to the corresponding N-hydroxyureas without extensive protecting group chemistry.

AB - Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In addition to primary and secondary aliphatic and aromatic amines, this method converts amino sugars to the corresponding N-hydroxyureas without extensive protecting group chemistry.

KW - N-Hydroxyureas

KW - nitric oxide

KW - nitric oxide donors

KW - Carbohydrates

KW - Hydrogenation

M3 - Article

SN - 0040-4039

SP - 8841

EP - 8843

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

A convenient method for the synthesis of N-hydroxyureas

Abstract

Keywords

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