The aza-Wittig reaction: an efficient tool for the construction of carbon–nitrogen double bonds

Palacios, Francisco; Alonso, C.; Aparicio, Domitila; Rubiales, Gloria; Santos, Jesús M. de los

doi:10.1016/j.tet.2006.09.048

Cited by 366 publications

(183 citation statements)

References 233 publications

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“…Some of them have shown good antineoplastic [31] and protein kinase inhibitor [32] activities. Also, heterocycles containing an imidazolone moiety exhibits various biological activities such as antibacterial and antifungal activities [33][34][35].…”

Section: Geometric Structurementioning

confidence: 99%

Vibrational spectroscopy investigation using M06-2X and B3LYP methods analysis on the structure of 2-Trifluoromethyl-10H-benzo[4,5]-imidazo[1,2-a]pyrimidin-4-one

Sert¹,

Mahendra²,

Chandra³

et al. 2014

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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h i g h l i g h t sThe FT-IR and Laser-Raman spectra of the title compound were recorded in solid phase. The optimized geometry and vibrational frequencies were calculated for the first time. The HOMO-LUMO energies and related molecular properties were evaluated. g r a p h i c a l a b s t r a c t a r t i c l e i n f o In this study, the experimental and theoretical vibrational frequencies of a newly synthesized bioactive agent namely, 2-Trifluoromethyl-10H-benzo[4,5]-imidazo[1,2-a]pyrimidin-4-one (TIP) have been investigated. The experimental FT-IR (4000-400 cm À1 ) and Laser-Raman spectra (4000-100 cm À1 ) of the molecule in solid phase have been recorded. The theoretical vibrational frequencies and the optimized geometric parameters (bond lengths and bond angles) have been calculated using density functional theory (DFT/B3LYP: Becke, 3-parameter, Lee-Yang-Parr) and M06-2X (the highly parametrized, empirical exchange correlation function) quantum chemical methods with 6-311++G(d,p) basis set by Gaussian 09W software, for the first time. The assignments of the vibrational frequencies have been done by potential energy distribution (PED) analysis using VEDA 4 software. The theoretical optimized geometric parameters and vibrational frequencies have been found to be in good agreement with the corresponding experimental data and results in the literature. In addition, the highest occupied molecular orbital (HOMO) energy, the lowest unoccupied molecular orbital (LUMO) energy and the other related molecular energy values of the compound have been investigated using the same theoretical calculations.

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Section: Geometric Structurementioning

confidence: 99%

Vibrational spectroscopy investigation using M06-2X and B3LYP methods analysis on the structure of 2-Trifluoromethyl-10H-benzo[4,5]-imidazo[1,2-a]pyrimidin-4-one

Sert¹,

Mahendra²,

Chandra³

et al. 2014

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…[42] It is well established that the reaction of iminophosphoranes with carbonyl compounds constitutes an excellent method for the construction of imino groups ('aza-Wittig' reaction). [44,45] To test this in the cyclobutenone series, 18 (R 1 ¼ iPr; R 2 ¼ Ph) was treated with (N-phenylimino)triphenylphosphorane and this gave the corresponding 21 in 89% yield. This compound was identical to the iminocyclobutenone obtained in 73% by the method outlined in Scheme 6.…”

Section: Synthesis Of 4-iminocyclobutenonesmentioning

confidence: 99%

“…Formation of 24 is assumed to involve initial attack of the iminophosporane on the more reactive carbonyl group of 18 to give 22. This zwitterionic intermediate, having a choice of an aza-Wittig [44,45] or aza-Peterson reaction, [49,50] eliminates trimethylsiloxide followed by dealkylation to give 24.…”

Section: Synthesis Of 4-iminocyclobutenonesmentioning

confidence: 99%

New Syntheses and Ring Expansion Reactions of Cyclobutenimines

et al. 2010

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Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein's reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively.

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“…[10][11][12][13][14][15] Recently we have been interested in the synthesis of quinazolinones, thienopyrimidinones and imidazolinones via aza-Wittig reaction, with the aim of evaluating their fungicidal activities. [16][17][18][19][20][21][22] Herein we wish to report a selective synthesis and fungicidal activities of 2-alkylamino-3-aryl-6-(1H-1,2,4-triazol-1-yl)-thieno [2,3-d]pyrimidin-4(3H)-ones via an iminophosphorane 3.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis and fungicidal activities of 2-alkylamino-6-(1H-1,2,4-triazol-1-yl)-thieno[2,3-d]pyrimidin-4(3H)-ones

Sun¹,

Wu²,

Wan³

et al. 2009

Arkivoc

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The carbodiimides 4, obtained from an aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with primary amines in the presence of catalytic amounts of sodium alkoxide to give selectively 2-alkylamino-3-aryl-6-(1H-1,2,4-triazol-1-yl)-thieno[2,3-d]-pyrimidin-4(3H)-ones 6 in good yields. Compounds 6 exhibit fungicidal activity; e.g., compound 6h showing the best inhibitive activity (92%) against Colletotrichum gossypii in 50 mg/L.

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The aza-Wittig reaction: an efficient tool for the construction of carbon–nitrogen double bonds

Cited by 366 publications

References 233 publications

Vibrational spectroscopy investigation using M06-2X and B3LYP methods analysis on the structure of 2-Trifluoromethyl-10H-benzo[4,5]-imidazo[1,2-a]pyrimidin-4-one

Vibrational spectroscopy investigation using M06-2X and B3LYP methods analysis on the structure of 2-Trifluoromethyl-10H-benzo[4,5]-imidazo[1,2-a]pyrimidin-4-one

New Syntheses and Ring Expansion Reactions of Cyclobutenimines

Efficient synthesis and fungicidal activities of 2-alkylamino-6-(1H-1,2,4-triazol-1-yl)-thieno[2,3-d]pyrimidin-4(3H)-ones

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