Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles

Arthur Y. Shaw; Jonathan A. McLaren; Gary S. Nichol; Christopher Hulme

doi:10.1016/j.tetlet.2012.03.033

Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles

Arthur Y. Shaw
, Jonathan A. McLaren
, Gary S. Nichol
, Christopher Hulme

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

18 Scopus citations

Abstract

This report discloses a novel concise synthesis of a series of 3-hydroxypyrazoles 5 via a tandem Ugi/debenzylation /hydrazine-mediated cyclization sequence. Herein, n-butyl isocyanide 4b was utilized as an alternative to classical convertible isocyanides enabling high yielding hydrazine-mediated cyclization. Taken together, a novel class of 3-hydroxypyrazoles 5a-5i was synthesized with a potential to be of interest in future library enrichment strategies.

Original language	English (US)
Pages (from-to)	2592-2594
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2012.03.033
State	Published - May 23 2012

Keywords

3-Hydroxypyrazole
Hydrazine-mediated cyclization
Multicomponent reaction
Ugi reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.03.033

Cite this

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title = "Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles",

abstract = "This report discloses a novel concise synthesis of a series of 3-hydroxypyrazoles 5 via a tandem Ugi/debenzylation /hydrazine-mediated cyclization sequence. Herein, n-butyl isocyanide 4b was utilized as an alternative to classical convertible isocyanides enabling high yielding hydrazine-mediated cyclization. Taken together, a novel class of 3-hydroxypyrazoles 5a-5i was synthesized with a potential to be of interest in future library enrichment strategies.",

keywords = "3-Hydroxypyrazole, Hydrazine-mediated cyclization, Multicomponent reaction, Ugi reaction",

author = "Shaw, \{Arthur Y.\} and McLaren, \{Jonathan A.\} and Nichol, \{Gary S.\} and Christopher Hulme",

note = "Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding (1RC2MH090878-01). Particular thanks to N. Schechter (PSM) for copy editing. ",

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doi = "10.1016/j.tetlet.2012.03.033",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles

AU - Shaw, Arthur Y.

AU - McLaren, Jonathan A.

AU - Nichol, Gary S.

AU - Hulme, Christopher

N1 - Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding (1RC2MH090878-01). Particular thanks to N. Schechter (PSM) for copy editing.

PY - 2012/5/23

Y1 - 2012/5/23

N2 - This report discloses a novel concise synthesis of a series of 3-hydroxypyrazoles 5 via a tandem Ugi/debenzylation /hydrazine-mediated cyclization sequence. Herein, n-butyl isocyanide 4b was utilized as an alternative to classical convertible isocyanides enabling high yielding hydrazine-mediated cyclization. Taken together, a novel class of 3-hydroxypyrazoles 5a-5i was synthesized with a potential to be of interest in future library enrichment strategies.

AB - This report discloses a novel concise synthesis of a series of 3-hydroxypyrazoles 5 via a tandem Ugi/debenzylation /hydrazine-mediated cyclization sequence. Herein, n-butyl isocyanide 4b was utilized as an alternative to classical convertible isocyanides enabling high yielding hydrazine-mediated cyclization. Taken together, a novel class of 3-hydroxypyrazoles 5a-5i was synthesized with a potential to be of interest in future library enrichment strategies.

KW - 3-Hydroxypyrazole

KW - Hydrazine-mediated cyclization

KW - Multicomponent reaction

KW - Ugi reaction

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DO - 10.1016/j.tetlet.2012.03.033

M3 - Article

AN - SCOPUS:84859773899

SN - 0040-4039

VL - 53

SP - 2592

EP - 2594

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles

Abstract

Keywords

ASJC Scopus subject areas

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