Literature DB >> 32397450

Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products.

Farid N Naghiyev1, Jonathan Cisterna2, Ali N Khalilov1,3, Abel M Maharramov1, Rizvan K Askerov1, Khammed A Asadov1, Ibrahim G Mamedov1, Khaver S Salmanli1, Alejandro Cárdenas4, Ivan Brito2.   

Abstract

We report an unprecedented multicomponent reaction of acetoacetanilide with malononitrile leading to a structurally novel bicyclic product (9) in a high yield. The structure has been confirmed by X-ray crystallography and comparative Hirshfeld surface analysis of 5-cyano-2-hydroxy-2-methyl-N-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide 2, 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide 4 and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-ylidene)-N-phenylacetamide 9.

Entities:  

Keywords:  Hirshfeld surface analysis; X-ray analysis; acetoacetanilide; multicomponent reaction

Mesh：

Substances：

Year:  2020        PMID： 32397450      PMCID： PMC7248728          DOI： 10.3390/molecules25092235

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  10 in total

1.  Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules.

Authors:  Julian Tirado-Rives; William L Jorgensen
Journal:  J Chem Theory Comput       Date:  2008-02       Impact factor: 6.006

2.  Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces.

Authors:  Joshua J McKinnon; Dylan Jayatilaka; Mark A Spackman
Journal:  Chem Commun (Camb)       Date:  2007-10-07       Impact factor: 6.222

3.  Efficient one-pot synthesis of substituted pyridines through multicomponent reaction.

Authors:  Xin Xin; Yan Wang; Santosh Kumar; Xu Liu; Yingjie Lin; Dewen Dong
Journal:  Org Biomol Chem       Date:  2010-05-18       Impact factor: 3.876

4.  Pyridone alkaloids from a marine-derived fungus, Stagonosporopsis cucurbitacearum, and their activities against azole-resistant Candida albicans.

Authors:  Asami Haga; Hiroki Tamoto; Masahiro Ishino; Eriko Kimura; Takashi Sugita; Kaoru Kinoshita; Kunio Takahashi; Motoo Shiro; Kiyotaka Koyama
Journal:  J Nat Prod       Date:  2013-03-15       Impact factor: 4.050

5.  Synthesis of pyran and pyranone natural products.

Authors:  Christopher D Donner; Melvyn Gill; Leonie M Tewierik
Journal:  Molecules       Date:  2004-05-31       Impact factor: 4.411

6.  Isoquinoline-based analogs of the cancer drug clinical candidate tipifarnib as anti-Trypanosoma cruzi agents.

Authors:  Naveen Kumar Chennamaneni; Jenifer Arif; Frederick S Buckner; Michael H Gelb
Journal:  Bioorg Med Chem Lett       Date:  2009-10-13       Impact factor: 2.823

7.  Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4H-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities.

Authors:  Rasha Abdallah Azzam; Rafat Milad Mohareb
Journal:  Chem Pharm Bull (Tokyo)       Date:  2015       Impact factor: 1.645

8.  Synthesis and antimicrobial properties of 2H-pyran-3(6H)-one derivatives and related compounds.

Authors:  M P Georgiadis; E A Couladouros; A K Delitheos
Journal:  J Pharm Sci       Date:  1992-11       Impact factor: 3.534

Review 9.  An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883

10.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172
  10 in total
  9 in total

1.  Crystal structure and Hirshfeld surface analysis of 5-(5-phenyl-1,2-oxazol-3-yl)-1,3,4-thia-diazol-2-amine.

Authors:  Evgeniya V Nikitina; Sevim Türktekin Çelikesir; Mehmet Akkurt; Sergey K Petkevich; Ekaterina A Akishina; Victor N Khrustalev; Sixberth Mlowe
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-03-31

2.  Crystal structure and Hirshfeld surface analysis of 2-amino-4-(4-meth-oxy-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Authors:  Khammed A Asadov; Victor N Khrustalev; Ekaterina V Dobrokhotova; Mehmet Akkurt; Afet T Huseynova; Anzurat A Akobirshoeva; Elnur Z Huseynov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-02-22

3.  Crystal structure and Hirshfeld surface analysis of 5-acetyl-2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Authors:  Ibrahim G Mamedov; Victor N Khrustalev; Mehmet Akkurt; Anton P Novikov; Ayten R Asgarova; Khatira N Aliyeva; Anzurat A Akobirshoeva
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-02-03

4.  Crystal structure and Hirshfeld surface analysis of 2-(4-amino-6-phenyl-1,2,5,6-tetra-hydro-1,3,5-triazin-2-yl-idene)malono-nitrile di-methyl-formamide hemisolvate.

Authors:  Ibadulla Mahmudov; Zeliha Atioğlu; Mehmet Akkurt; Yusif Abdullayev; Afsun Sujayev; Ajaya Bhattarai
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-07-12

5.  Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenyl-butan-2-yl)-2-hy-droxy-2-methyl-4-phenyl-cyclo-hexane-1,1-dicarbo-nitrile.

Authors:  Farid N Naghiyev; Victor N Khrustalev; Ekaterina V Dobrokhotova; Mehmet Akkurt; Ali N Khalilov; Ajaya Bhattarai; İbrahim G Mamedov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-05-13

6.  Crystal structures and Hirshfeld surface analyses of 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemi-hydrate and 1,6-di-amino-2-oxo-4-phenyl-1,2-di-hydro-pyridine-3,5-dicarbo-nitrile.

Authors:  Farid N Naghiyev; Victor N Khrustalev; Nikolai U Venskovsky; Tatiana A Tereshina; Ali N Khalilov; Mehmet Akkurt; Ajaya Bhattarai; İbrahim G Mamedov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-07-26

7.  Crystal structure and Hirshfeld surface analysis of ethyl 2'-amino-5-bromo-3'-cyano-6'-methyl-2-oxo-spiro-[indoline-3,4'-pyran]-5'-carboxyl-ate.

Authors:  Farid N Naghiyev; Victor N Khrustalev; Nikolai U Venskovsky; Mehmet Akkurt; Ali N Khalilov; Ajaya Bhattarai; İbrahim G Mamedov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-08-26

8.  Crystal structure and Hirshfeld surface analysis of N-{[5-(4-methyl-phen-yl)-1,2-oxazol-3-yl]meth-yl}-1-phenyl-N-(prop-2-en-1-yl)methane-sulfonamide.

Authors:  Victor N Khrustalev; Sevim Türktekin Çelikesir; Mehmet Akkurt; Irina A Kolesnik; Vladimir I Potkin; Sixberth Mlowe
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-05-17

9.  Crystal structure and Hirshfeld surface analysis of 5-amino-5'-bromo-2'-oxo-2,3-di-hydro-1H-spiro-[imidazo[1,2-a]pyridine-7,3'-indoline]-6,8-dicarbo-nitrile dimethyl sulfoxide disolvate.

Authors:  Farid N Naghiyev; Victor N Khrustalev; Anton P Novikov; Mehmet Akkurt; Rovnag M Rzayev; Anzurat A Akobirshoeva; Ibrahim G Mamedov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-05-10
  9 in total

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