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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 11: 3704 - 3713

DOI: https://doi.org/10.6023/cjoc202204033

ARTICLES

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Nucleophilic Addition of Two Molecules of Nitroalkanes to Diazo Compounds: Synthesis of Highly Functionalized Hydrazones and Tetrahydropyridazines

  • Xiaoyong Zhang ,
  • Lili Yu ,
  • Junfang Gao ,
  • Yue Gong ,
  • Yulong Zhao
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  • aDepartment of Chemistry, Baotou Teachers’ College, Baotou, Inner Mongolia 014030
    bJilin Provincial Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024
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Received date: 2022-04-13

  Revised date: 2022-07-24

  Online published: 2022-08-10

Supported by

National Natural Sciences Foundation of China(21871044); National Natural Sciences Foundation of China(22165022)

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Abstract

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted intermolecular addition reaction two molecules of nitroalkanes to diazo compounds has been developed, in which diazo compounds sereve as the efficient N-terminal electrophiles. The reaction provides two new and highly efficient methods for the construction of functionalized hydrazones and tetrahydropyridazines bearing the structure feature of nitroalkanes from readily available starting materials. The reaction involves a sequential intermolecular nucleophilic addition/elimination/intermolecular Aza-Henry reaction/intramolecular cyclization procedure where two or three adjacent stereocenters are created simultaneously in one-pot manner.

Key words： diazo compound; N-terminal electrophile; nitroalkane; hydrazone; tetrahydropyridazine

Cite this article

Xiaoyong Zhang , Lili Yu , Junfang Gao , Yue Gong , Yulong Zhao . 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Nucleophilic Addition of Two Molecules of Nitroalkanes to Diazo Compounds: Synthesis of Highly Functionalized Hydrazones and Tetrahydropyridazines[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3704 -3713 . DOI: 10.6023/cjoc202204033

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