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Heterocyclic Communications

, volume 24 , issue 1 , pages 31-35

Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement

Nasrin Karimi ¹

Davoodnia Abolghasem ²

Mehdi Pordel ¹

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Department of Chemistry , Mashhad Branch, Islamic Azad University , Mashhad , 91756-87119 Iran |

Department of Chemistry , Mashhad Branch, Islamic Azad University , Mashhad , 91756-87119 Iran , e-mail: |

Publication type: Journal Article

Publication date: 2018-01-19

Walter de Gruyter

Heterocyclic Communications

scimago Q3

wos Q3

SJR: 0.292

CiteScore: 3.4

Impact factor: 1.5

ISSN: 07930283, 21910197

DOI: 10.1515/hc-2017-0228

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Organic Chemistry

Abstract

The reaction of 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles with excess aliphatic carboxylic acids in the presence of phosphoryl chloride (POCl₃) afforded new 2-alkyl-5-aryl-8,8-dimethyl-8,9-dihydro-3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones in high yields. The suggested mechanism involves a tandem intramolecular Pinner/Dimroth rearrangement. The synthesized compounds were characterized by infrared (IR), proton nuclear magnetic resonance (¹H NMR), carbon-13 nuclear magnetic resonance (¹³C NMR) and elemental analysis.

Found

1 citation

Churakov Andrei

PhD in Chemistry

557 publications, 7 120 citations, 14 reviews

h-index: 38

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

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Karimi N., Abolghasem D., Pordel M. Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement // Heterocyclic Communications. 2018. Vol. 24. No. 1. pp. 31-35.

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RIS Copy

TY - JOUR

DO - 10.1515/hc-2017-0228

UR - https://doi.org/10.1515/hc-2017-0228

TI - Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement

T2 - Heterocyclic Communications

AU - Karimi, Nasrin

AU - Abolghasem, Davoodnia

AU - Pordel, Mehdi

PY - 2018

DA - 2018/01/19

PB - Walter de Gruyter

SP - 31-35

IS - 1

VL - 24

SN - 0793-0283

SN - 2191-0197

ER -

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@article{2018_Karimi,

author = {Nasrin Karimi and Davoodnia Abolghasem and Mehdi Pordel},

title = {Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement},

journal = {Heterocyclic Communications},

year = {2018},

volume = {24},

publisher = {Walter de Gruyter},

month = {jan},

url = {https://doi.org/10.1515/hc-2017-0228},

number = {1},

pages = {31--35},

doi = {10.1515/hc-2017-0228}

}

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Karimi, Nasrin, et al. “Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement.” Heterocyclic Communications, vol. 24, no. 1, Jan. 2018, pp. 31-35. https://doi.org/10.1515/hc-2017-0228.

Publisher

Walter de Gruyter

Journal

Heterocyclic Communications

scimago Q3

wos Q3

SJR

0.292

CiteScore

3.4

Impact factor

1.5

ISSN

07930283 (Print)

21910197 (Electronic)