Microwave-assisted new conversion of friedländer reaction based on o-aminocyanopyrazole and cyclohexanone

Li Jun Zhang; Jia Rong Li; Jin Nan Chen; Da Xin Shi; Qi Zhang

Microwave-assisted new conversion of friedländer reaction based on o-aminocyanopyrazole and cyclohexanone

Li Jun Zhang^*, Jia Rong Li, Jin Nan Chen, Da Xin Shi, Qi Zhang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

Abstract

To investigate the reaction of o-aminocyanopyrazole and cyclohexanone under microwave irradiation, 5-amino-4-cyano-1-phenylpyrazole and cyclohexanone were dispersed in different solvents, promoted by Lewis acid catalysts, and reacted in Biotage microwave reactor for different time and temperature. Incorporated with the normal Friedlander cyclocondensed compound, 1H-quinolino-[3, 4-b]-pyrazole, new product 1H-pyrazolo[3, 4-d]pyrimidin-4(5H)-one was conveniently synthesized under microwave irradiation via new conversion of Friedlander annulation like using traditional heating. All the new products were characterized by IR, MS, ¹H NMR, ¹³C NMR and elemental analysis. The study indicated that heating with microwaves versus, compared with classical conditions, show higher yielding, and was cleaner and faster.

Original language	English
Pages (from-to)	25-28
Number of pages	4
Journal	Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology
Volume	27
Issue number	SUPPL. 2
Publication status	Published - Dec 2007

Keywords

Cyclization
Friedlander reaction
Microwave
Pyrazolo[3, 4-d]pyrimidin-4(5H)-one

Cite this

@article{93881823ebd7462187a4349bdf193347,

title = "Microwave-assisted new conversion of friedl{\"a}nder reaction based on o-aminocyanopyrazole and cyclohexanone",

abstract = "To investigate the reaction of o-aminocyanopyrazole and cyclohexanone under microwave irradiation, 5-amino-4-cyano-1-phenylpyrazole and cyclohexanone were dispersed in different solvents, promoted by Lewis acid catalysts, and reacted in Biotage microwave reactor for different time and temperature. Incorporated with the normal Friedlander cyclocondensed compound, 1H-quinolino-[3, 4-b]-pyrazole, new product 1H-pyrazolo[3, 4-d]pyrimidin-4(5H)-one was conveniently synthesized under microwave irradiation via new conversion of Friedlander annulation like using traditional heating. All the new products were characterized by IR, MS, 1H NMR, 13C NMR and elemental analysis. The study indicated that heating with microwaves versus, compared with classical conditions, show higher yielding, and was cleaner and faster.",

keywords = "Cyclization, Friedlander reaction, Microwave, Pyrazolo[3, 4-d]pyrimidin-4(5H)-one",

author = "Zhang, {Li Jun} and Li, {Jia Rong} and Chen, {Jin Nan} and Shi, {Da Xin} and Qi Zhang",

year = "2007",

month = dec,

language = "English",

volume = "27",

pages = "25--28",

journal = "Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology",

issn = "1001-0645",

publisher = "Beijing Institute of Technology",

number = "SUPPL. 2",

}

TY - JOUR

T1 - Microwave-assisted new conversion of friedländer reaction based on o-aminocyanopyrazole and cyclohexanone

AU - Zhang, Li Jun

AU - Li, Jia Rong

AU - Chen, Jin Nan

AU - Shi, Da Xin

AU - Zhang, Qi

PY - 2007/12

Y1 - 2007/12

N2 - To investigate the reaction of o-aminocyanopyrazole and cyclohexanone under microwave irradiation, 5-amino-4-cyano-1-phenylpyrazole and cyclohexanone were dispersed in different solvents, promoted by Lewis acid catalysts, and reacted in Biotage microwave reactor for different time and temperature. Incorporated with the normal Friedlander cyclocondensed compound, 1H-quinolino-[3, 4-b]-pyrazole, new product 1H-pyrazolo[3, 4-d]pyrimidin-4(5H)-one was conveniently synthesized under microwave irradiation via new conversion of Friedlander annulation like using traditional heating. All the new products were characterized by IR, MS, 1H NMR, 13C NMR and elemental analysis. The study indicated that heating with microwaves versus, compared with classical conditions, show higher yielding, and was cleaner and faster.

AB - To investigate the reaction of o-aminocyanopyrazole and cyclohexanone under microwave irradiation, 5-amino-4-cyano-1-phenylpyrazole and cyclohexanone were dispersed in different solvents, promoted by Lewis acid catalysts, and reacted in Biotage microwave reactor for different time and temperature. Incorporated with the normal Friedlander cyclocondensed compound, 1H-quinolino-[3, 4-b]-pyrazole, new product 1H-pyrazolo[3, 4-d]pyrimidin-4(5H)-one was conveniently synthesized under microwave irradiation via new conversion of Friedlander annulation like using traditional heating. All the new products were characterized by IR, MS, 1H NMR, 13C NMR and elemental analysis. The study indicated that heating with microwaves versus, compared with classical conditions, show higher yielding, and was cleaner and faster.

KW - Cyclization

KW - Friedlander reaction

KW - Microwave

KW - Pyrazolo[3, 4-d]pyrimidin-4(5H)-one

UR - http://www.scopus.com/inward/record.url?scp=40749127556&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:40749127556

SN - 1001-0645

VL - 27

SP - 25

EP - 28

JO - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

JF - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

IS - SUPPL. 2

ER -

Microwave-assisted new conversion of friedländer reaction based on o-aminocyanopyrazole and cyclohexanone

Abstract

Keywords

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