2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines

Yongying Jiang; Jun Zhao; Longqin Hu

doi:10.1016/S0040-4039(02)00891-2

2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines

Yongying Jiang, Jun Zhao, Longqin Hu

Ernest Mario School of Pharmacy, Medicinal Chemistry

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

18 Scopus citations

Abstract

2,2-Dimethyl-2-(o-nitrophenyl)acetyl group (DMNA) was explored as an assisted cleavage protecting group for amines and a one-step deprotection condition was developed for its efficient removal using hydrogenation in the presence of Pd-C or PtO₂ catalyst and 10% HOAc in MeOH. DMNA was found to be especially useful for the synthesis of gem-diamino compounds using Hofmann rearrangement.

Original language	English (US)
Pages (from-to)	4589-4592
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(02)00891-2
State	Published - Jun 28 2002

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines",

abstract = "2,2-Dimethyl-2-(o-nitrophenyl)acetyl group (DMNA) was explored as an assisted cleavage protecting group for amines and a one-step deprotection condition was developed for its efficient removal using hydrogenation in the presence of Pd-C or PtO2 catalyst and 10% HOAc in MeOH. DMNA was found to be especially useful for the synthesis of gem-diamino compounds using Hofmann rearrangement.",

author = "Yongying Jiang and Jun Zhao and Longqin Hu",

note = "Funding Information: We gratefully acknowledge the financial support of a pilot project grant from the Gallo Prostate Cancer Center of the Cancer Institute of New Jersey.",

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T1 - 2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines

AU - Jiang, Yongying

AU - Zhao, Jun

AU - Hu, Longqin

N1 - Funding Information: We gratefully acknowledge the financial support of a pilot project grant from the Gallo Prostate Cancer Center of the Cancer Institute of New Jersey.

PY - 2002/6/28

Y1 - 2002/6/28

N2 - 2,2-Dimethyl-2-(o-nitrophenyl)acetyl group (DMNA) was explored as an assisted cleavage protecting group for amines and a one-step deprotection condition was developed for its efficient removal using hydrogenation in the presence of Pd-C or PtO2 catalyst and 10% HOAc in MeOH. DMNA was found to be especially useful for the synthesis of gem-diamino compounds using Hofmann rearrangement.

AB - 2,2-Dimethyl-2-(o-nitrophenyl)acetyl group (DMNA) was explored as an assisted cleavage protecting group for amines and a one-step deprotection condition was developed for its efficient removal using hydrogenation in the presence of Pd-C or PtO2 catalyst and 10% HOAc in MeOH. DMNA was found to be especially useful for the synthesis of gem-diamino compounds using Hofmann rearrangement.

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U2 - 10.1016/S0040-4039(02)00891-2

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SN - 0040-4039

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EP - 4592

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines

Abstract

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