Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes

Asma Khazaee; Roya Jahanshahi; Sara Sobhani; Jørgen Skibsted; José Miguel Sansano

doi:10.1039/d0gc01274b

Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes

Asma Khazaee, Roya Jahanshahi, Sara Sobhani, Jørgen Skibsted, José Miguel Sansano

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

52 Citations (Scopus)

Abstract

Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.

Original language	English
Journal	Green Chemistry
Volume	22
Issue	14
Pages (from-to)	4604-4616
Number of pages	13
ISSN	1463-9262
DOIs	https://doi.org/10.1039/d0gc01274b
Publication status	Published - Jul 2020

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@article{37ee0c42694c43c19e96b492df038623,

title = "Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes",

abstract = "Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si\{1H\} and 13C\{1H\} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.",

author = "Asma Khazaee and Roya Jahanshahi and Sara Sobhani and J{\o}rgen Skibsted and Sansano, \{Jos{\'e} Miguel\}",

year = "2020",

month = jul,

doi = "10.1039/d0gc01274b",

language = "English",

volume = "22",

pages = "4604--4616",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

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Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes. / Khazaee, Asma; Jahanshahi, Roya; Sobhani, Sara et al.
In: Green Chemistry, Vol. 22, No. 14, 07.2020, p. 4604-4616.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes

AU - Khazaee, Asma

AU - Jahanshahi, Roya

AU - Sobhani, Sara

AU - Skibsted, Jørgen

AU - Sansano, José Miguel

PY - 2020/7

Y1 - 2020/7

N2 - Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.

AB - Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.

UR - https://www.scopus.com/pages/publications/85089067071

U2 - 10.1039/d0gc01274b

DO - 10.1039/d0gc01274b

M3 - Journal article

AN - SCOPUS:85089067071

SN - 1463-9262

VL - 22

SP - 4604

EP - 4616

JO - Green Chemistry

JF - Green Chemistry

IS - 14

ER -

Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4H -chromenes

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