1-Cyano-3-(1H)-1,2-benziodoxols: stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines

Viktor Zhdankin; Chris J. Kuehl; Alexei P. Krasutsky; Jason T. Bolz; Brian Mismash; Jessica K. Woodward; Angela J. Simonsen

doi:10.1016/0040-4039(95)01720-3

1-Cyano-3-(1H)-1,2-benziodoxols: stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines

Viktor Zhdankin
, Chris J. Kuehl
, Alexei P. Krasutsky
, Jason T. Bolz
, Brian Mismash
, Jessica K. Woodward
, Angela J. Simonsen

Chemistry & Biochemistry

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

126 Scopus citations

Abstract

Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.

Original language	English (US)
Pages (from-to)	7975-7978
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	44
DOIs	https://doi.org/10.1016/0040-4039(95)01720-3
State	Published - Oct 30 1995

Bibliographical note

Funding Information:
Acknowledgement. This work was supported by a Cottrell College Science Award of Research Corporation; a research grant from the National Science Foundation (NSFXHE-9505868); a grant from the Donors of The Petroleum Research Fund, administered by the ACS; the University of Minnesota Graduate School Grant-in-Aid; the UMD Department of Chemistry Summer 1995 Undergraduate Research Program, and a Fellowship Award for A.J.S. from the CURSOR program.

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@article{6cabbb8a908e4d0fb1f324498f77aacb,

title = "1-Cyano-3-(1H)-1,2-benziodoxols: stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines",

abstract = "Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.",

author = "Viktor Zhdankin and Kuehl, \{Chris J.\} and Krasutsky, \{Alexei P.\} and Bolz, \{Jason T.\} and Brian Mismash and Woodward, \{Jessica K.\} and Simonsen, \{Angela J.\}",

note = "Funding Information: Acknowledgement. This work was supported by a Cottrell College Science Award of Research Corporation; a research grant from the National Science Foundation (NSFXHE-9505868); a grant from the Donors of The Petroleum Research Fund, administered by the ACS; the University of Minnesota Graduate School Grant-in-Aid; the UMD Department of Chemistry Summer 1995 Undergraduate Research Program, and a Fellowship Award for A.J.S. from the CURSOR program.",

year = "1995",

month = oct,

day = "30",

doi = "10.1016/0040-4039(95)01720-3",

language = "English (US)",

volume = "36",

pages = "7975--7978",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "44",

}

TY - JOUR

T1 - 1-Cyano-3-(1H)-1,2-benziodoxols

T2 - stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines

AU - Zhdankin, Viktor

AU - Kuehl, Chris J.

AU - Krasutsky, Alexei P.

AU - Bolz, Jason T.

AU - Mismash, Brian

AU - Woodward, Jessica K.

AU - Simonsen, Angela J.

N1 - Funding Information: Acknowledgement. This work was supported by a Cottrell College Science Award of Research Corporation; a research grant from the National Science Foundation (NSFXHE-9505868); a grant from the Donors of The Petroleum Research Fund, administered by the ACS; the University of Minnesota Graduate School Grant-in-Aid; the UMD Department of Chemistry Summer 1995 Undergraduate Research Program, and a Fellowship Award for A.J.S. from the CURSOR program.

PY - 1995/10/30

Y1 - 1995/10/30

N2 - Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.

AB - Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylary lamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.

UR - https://www.scopus.com/pages/publications/0028792315

UR - https://www.scopus.com/pages/publications/0028792315#tab=citedBy

U2 - 10.1016/0040-4039(95)01720-3

DO - 10.1016/0040-4039(95)01720-3

M3 - Article

AN - SCOPUS:0028792315

SN - 0040-4039

VL - 36

SP - 7975

EP - 7978

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

1-Cyano-3-(1H)-1,2-benziodoxols: stable cyanoiodinanes and efficient reagents for direct N-alkyl cyanation of N,N-dialkylarylamines

Abstract

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