Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Koppanathi Nagaraju; Ramani Gurubrahamam; Ramani Gurubrahamam; Kwunmin Chen

doi:10.1021/acs.joc.0c00431

Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Koppanathi Nagaraju, Ramani Gurubrahamam, Ramani Gurubrahamam, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

16 Citations (Scopus)

Abstract

To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

Original language	English
Pages (from-to)	7060-7067
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	85
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.0c00431
Publication status	Published - 2020 Jun 5

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.0c00431

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title = "Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives",

abstract = "To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Br{\o}nsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).",

author = "Koppanathi Nagaraju and Ramani Gurubrahamam and Ramani Gurubrahamam and Kwunmin Chen",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jun,

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doi = "10.1021/acs.joc.0c00431",

language = "English",

volume = "85",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T1 - Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

AU - Nagaraju, Koppanathi

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2020/6/5

Y1 - 2020/6/5

N2 - To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

AB - To construct multisubstituted seven-membered nitrogenous heterocyclic scaffolds, an efficient method, employing 2-aminoaryl N-monosubstituted hydrazones and 2-oxo-3-butenoates under Brønsted acid catalysis, has been developed. This strategy highlights the umpolung reactivity of 2-aminobenzaldehyde arylhydrazones toward 2-oxo-3-butenoates to afford (E)-diazoaryl-benzo[b]azepine derivatives in excellent yields (89-99%) and with high diastereoselectivities (>19:1 dr).

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DO - 10.1021/acs.joc.0c00431

M3 - Article

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SN - 0022-3263

VL - 85

SP - 7060

EP - 7067

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Abstract

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CCDC 1940881: Experimental Crystal Structure Determination

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Organocatalytic Diastereoselective Synthesis of Diazoaryl-benzo[b]azepine Derivatives

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1940881: Experimental Crystal Structure Determination

Cite this