One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)- ones

Mingxing Liu; Jiarong Li; Shu Chen; Danfei Huang; Hongxin Chai; Qi Zhang; Daxin Shi

doi:10.1039/c4ra05346j

One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)- ones

Mingxing Liu, Jiarong Li, Shu Chen, Danfei Huang, Hongxin Chai, Qi Zhang, Daxin Shi^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

12 Citations (Scopus)

Abstract

An efficient N-heterocyclic carbene-assisted one-pot reaction for the synthesis of 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 2-(ethoxymethylene)malononitrile, guanidines (or amidines) and ketones (or aldehydes) has been developed. This highly efficient method includes a series of conversions such as Michael addition, cyclisation, isomerization, aromatization, then nucleophilic attack and Dimroth rearrangement. And it avoids complicated reagents and multiple steps.

Original language	English
Pages (from-to)	35629-35634
Number of pages	6
Journal	RSC Advances
Volume	4
Issue number	67
DOIs	https://doi.org/10.1039/c4ra05346j
Publication status	Published - 2014

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title = "One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)- ones",

abstract = "An efficient N-heterocyclic carbene-assisted one-pot reaction for the synthesis of 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 2-(ethoxymethylene)malononitrile, guanidines (or amidines) and ketones (or aldehydes) has been developed. This highly efficient method includes a series of conversions such as Michael addition, cyclisation, isomerization, aromatization, then nucleophilic attack and Dimroth rearrangement. And it avoids complicated reagents and multiple steps.",

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T1 - One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)- ones

AU - Liu, Mingxing

AU - Li, Jiarong

AU - Chen, Shu

AU - Huang, Danfei

AU - Chai, Hongxin

AU - Zhang, Qi

AU - Shi, Daxin

PY - 2014

Y1 - 2014

N2 - An efficient N-heterocyclic carbene-assisted one-pot reaction for the synthesis of 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 2-(ethoxymethylene)malononitrile, guanidines (or amidines) and ketones (or aldehydes) has been developed. This highly efficient method includes a series of conversions such as Michael addition, cyclisation, isomerization, aromatization, then nucleophilic attack and Dimroth rearrangement. And it avoids complicated reagents and multiple steps.

AB - An efficient N-heterocyclic carbene-assisted one-pot reaction for the synthesis of 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 2-(ethoxymethylene)malononitrile, guanidines (or amidines) and ketones (or aldehydes) has been developed. This highly efficient method includes a series of conversions such as Michael addition, cyclisation, isomerization, aromatization, then nucleophilic attack and Dimroth rearrangement. And it avoids complicated reagents and multiple steps.

UR - http://www.scopus.com/inward/record.url?scp=84906544420&partnerID=8YFLogxK

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DO - 10.1039/c4ra05346j

M3 - Article

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VL - 4

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EP - 35634

JO - RSC Advances

JF - RSC Advances

IS - 67

ER -

One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)- ones

Abstract

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