Startseite Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines
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Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines

  • Mehri Fattahi , Abolghasem Davoodnia EMAIL logo , Mehdi Pordel , S. Ali Beyramabadi und Niloofar Tavakoli-Hoseini
Veröffentlicht/Copyright: 5. Juli 2018
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 73 Heft 8

Abstract

Reaction of N-alkyl-2-imino-2H-chromene-3-carboxamides with dimethyl acetylenedicarboxylate (DMAD) in the presence of sodium carbonate as catalyst in refluxing ethanol gave new tricyclic products identified as methyl 3-alkyl-2-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-chromeno[2,3-d]pyrimidine-2-carboxylates. In the absence of sodium carbonate, dimethyl 2-((E)-3-(alkylcarbamoyl)-2H-chromen-2-ylideneamino)fumarates were isolated as intermediates. These intermediates could be successfully converted to the same new tricyclic products by heating in ethanol containing sodium carbonate. All new synthetic compounds were characterized on the basis of their FT-IR, 1H and 13C NMR spectra, and microanalytical data. To identify the correct stereoisomer of the intermediates, in one case a 2D nuclear Overhauser effect (2D-NOESY) spectrum together with density functional theory (DFT) calculation at the B3LYP/6-311+G(d,p) level of theory was used.

Keywords: 2D-NOESY; chromeno[2,3-d]pyrimidines; DFT; DMAD; sodium carbonate

Acknowledgment

We gratefully acknowledge the financial support from the Islamic Azad University, Mashhad Branch, Iran.

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Supplementry Material:

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2018-0042).

Received: 2018-02-17
Accepted: 2018-04-22
Published Online: 2018-07-05
Published in Print: 2018-08-28

©2018 Walter de Gruyter GmbH, Berlin/Boston

Artikel in diesem Heft

  1. Frontmatter
  2. In this Issue
  3. The lanthanide hydride oxides SmHO and HoHO
  4. Longiflorol, a bergenin α-d-apioside from the stem bark of Diospyros longiflora, and its antioxidant activity
  5. An expedient synthesis of 6-amino-5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(aryl)methyl]-1,3-dimethyl-2,4,6(1H,3H)-pyrimidinedione derivatives using Fe3O4@TiO2 nanocomposite as an efficient, magnetically separable, and reusable catalyst
  6. Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
  7. Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines
  8. The 3D supramolecular architecture of copper(II) 6-methyl-2-pyridone-4-carboxylate: synthesis, structure, magnetic behavior and DFT studies
  9. Synthesis, crystal structure, and magnetic properties of the complex [(CH3)3NH]2 [Co(NCS)4]
  10. π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one
  11. Oxidative coupling of cycloalkanones with 3-(pyridin-2-yl)-1,2,4-triazinone coordinated to Pd(II)
  12. Influence of high-energy ball milling and additives on the formation of sphere-like α-Al2O3 powder by high-temperature calcination
  13. Encapsulation of ferrocenes by hydrogen-bonded pyrogallol[4]arene dimers
  14. Syntheses and crystal structures of guanidine hydrochlorides with two Schiff base functions as efficient colorimetric and selective sensors for fluoride
https://doi.org/10.1515/znb-2018-0042
Schlagwörter für diesen Artikel
2D-NOESY; chromeno[2,3-d]pyrimidines; DFT; DMAD; sodium carbonate

Artikel in diesem Heft

  1. Frontmatter
  2. In this Issue
  3. The lanthanide hydride oxides SmHO and HoHO
  4. Longiflorol, a bergenin α-d-apioside from the stem bark of Diospyros longiflora, and its antioxidant activity
  5. An expedient synthesis of 6-amino-5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(aryl)methyl]-1,3-dimethyl-2,4,6(1H,3H)-pyrimidinedione derivatives using Fe3O4@TiO2 nanocomposite as an efficient, magnetically separable, and reusable catalyst
  6. Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
  7. Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines
  8. The 3D supramolecular architecture of copper(II) 6-methyl-2-pyridone-4-carboxylate: synthesis, structure, magnetic behavior and DFT studies
  9. Synthesis, crystal structure, and magnetic properties of the complex [(CH3)3NH]2 [Co(NCS)4]
  10. π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one
  11. Oxidative coupling of cycloalkanones with 3-(pyridin-2-yl)-1,2,4-triazinone coordinated to Pd(II)
  12. Influence of high-energy ball milling and additives on the formation of sphere-like α-Al2O3 powder by high-temperature calcination
  13. Encapsulation of ferrocenes by hydrogen-bonded pyrogallol[4]arene dimers
  14. Syntheses and crystal structures of guanidine hydrochlorides with two Schiff base functions as efficient colorimetric and selective sensors for fluoride
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