Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones

Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc

doi:10.1039/D0RA04345A

Publisher's PDF

Katso/Avaa

753.3 Kb

Lataukset:

Show download details Hide download details

Said, A. I., Palkó, M., Haukka, M., & Fülöp, F. (2020). Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones. RSC Advances, 10(56), 33937-33943. https://doi.org/10.1039/D0RA04345A

Julkaistu sarjassa

RSC Advances

Tekijät

Said, Awad I. |

Palkó, Márta |

Haukka, Matti |

Fülöp, Ferenc

Päivämäärä

2020

Oppiaine

Epäorgaaninen kemia Epäorgaaninen ja analyyttinen kemia Inorganic Chemistry Inorganic and Analytical Chemistry

Tekijänoikeudet

Reactions of diastereochemically varied norbornene-condensed 2-thioxopyrimidin-4-ones6and10with variously functionalized hydrazonoyl chlorides2a-hgave regioselectively angular norbornene-based [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones7a-hand11a,c-e, respectively. Thermal retro Diels-Alder (RDA) reaction of7a-hand11a,c-eresulted in the target compounds4a-has single products. On the other hand, reactions of thiouracil1and hydrozonoyl chlorides2a-egave regioselectively [1,2,4]triazolo[4,3-a]pyrimidinone-5(1H)-ones3a-e. The opposite regioselectivity of thiouracil1and norbornene-condensed 2-thioxopyrimidin-4-ones6and10was attributed to electronic factors according to DFT calculations. The angular structure of norbornene based [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones was confirmed by single crystal X-ray crystallography.

Julkaisija

Royal Society of Chemistry

ISSN Hae Julkaisufoorumista

2046-2069

Lisätietoja rahoituksesta

We are grateful to the Hungarian Research Foundation (OTKA No. K 115731). The financial support of the GINOP-2.3.2-15-2016-00038 project is acknowledged. Ministry of Human Capacities, Hungary grant 20391-3/2018/FEKUSTRAT is acknowledged. In addition, Tempus Public Foundation is also acknowledged for its financial support (No. AK-00167-002/2019).

Lisenssi

Ellei muuten mainita, aineiston lisenssi on CC BY-NC 4.0

Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.

Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides : Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones

Said, Awad I.; Palkó, Márta; Haukka, Matti; Fülöp, Ferenc (MDPI, 2020)

The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones was performed. The 2-thioxopyrimidin-4-ones used in the synthesis reacted with ...
Synthesis and biological evaluation of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues

El Haimer, Mohamed; Palkó, Márta; Haukka, Matti; Gajdács, Márió; Zupkó, István; Fülöp, Ferenc (Royal Society of Chemistry (RSC), 2021)

Derivatives of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepinone and its cycloalkane and cycloalkene condensed analogues have been conveniently synthesized through a three-step reaction ...
Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin : X-ray Crystal Structure and Computational Investigations

Altowyan, Mezna Saleh; Haukka, Matti; Soliman, Saied M.; Barakat, Assem; Boraei, Ahmed T. A.; Sopaih, Manar (MDPI AG, 2023)

The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very ...
Synthesis, characterization, crystal structures and biological screening of 4-amino quinazoline sulfonamide derivatives

Kumar, A. Sunil; Kudva, Jyothi; Lahtinen, Manu; Peuronen, Anssi; Sadashiva, Rajitha; Naral, Damodara (Elsevier BV, 2019)

Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c) were synthesized by reacting (E)-N'-(2-cyanophenyl)-N,N-dimethyl formamidine (6) with different 4- amino-N-(phenyl)benzenesulfonamides ...
Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives : X-ray Single Crystal Structure and Hirshfeld Analyses

Boraei, Ahmed T. A.; Haukka, Matti; Sopaih, Manar; Al-Majid, Abdullah Mohammed; Soliman, Saied M.; Barakat, Assem; Sarhan, Ahmed A. M. (MDPI AG, 2022)

A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tet ...