Literature DB >> 23588897

Recent progress in asymmetric Biginelli reaction.

Majid M Heravi1, Shima Asadi, Boshra Malekzadeh Lashkariani.   

Abstract

The Biginelli reaction, which involves the interaction of ethyl acetoacetate, urea, and an appropriate aryl aldehyde, was first discovered by Pietro Biginelli about 120 years ago. The Biginelli products (3,4-dihydropyrimidin-2(1H)-ones) are interesting materials due to their significant pharmacological and structural profiles. In the last decades, the asymmetric synthesis as a powerful tool has an effective impact on the Biginelli products and has increased their potencies and applications as drugs. Having the importance of this subject in mind, in this review we wish to present the recent rapid progress of asymmetric Biginelli reaction.

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Year:  2013        PMID: 23588897     DOI: 10.1007/s11030-013-9439-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  47 in total

1.  New generation ionic liquids: cations derived from amino acids.

Authors:  Guo-hong Tao; Ling He; Ning Sun; Yuan Kou
Journal:  Chem Commun (Camb)       Date:  2005-06-09       Impact factor: 6.222

2.  Organocatalyzed asymmetric reactions via microwave activation.

Authors:  Sarah Mossé; Alexandre Alexakis
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

3.  In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective alpha(1A) receptor antagonists for the treatment of benign prostatic hyperplasia.

Authors:  J C Barrow; P G Nantermet; H G Selnick; K L Glass; K E Rittle; K F Gilbert; T G Steele; C F Homnick; R M Freidinger; R W Ransom; P Kling; D Reiss; T P Broten; T W Schorn; R S Chang; S S O'Malley; T V Olah; J D Ellis; A Barrish; K Kassahun; P Leppert; D Nagarathnam; C Forray
Journal:  J Med Chem       Date:  2000-07-13       Impact factor: 7.446

4.  Highly enantioselective organocatalytic Biginelli reaction.

Authors:  Xiao-Hua Chen; Xiao-Ying Xu; Hua Liu; Lin-Feng Cun; Liu-Zhu Gong
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

5.  Bifunctional primary amine-thiourea-TfOH (BPAT·TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimidines.

Authors:  Yangyun Wang; Jipan Yu; Zhiwei Miao; Ruyu Chen
Journal:  Org Biomol Chem       Date:  2011-03-11       Impact factor: 3.876

6.  Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates.

Authors:  Naidu S Chowdari; D B Ramachary; Carlos F Barbas
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

Review 7.  A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis.

Authors:  Maksim A Kolosov; Valeriy D Orlov; Dmitriy A Beloborodov; Victor V Dotsenko
Journal:  Mol Divers       Date:  2008-12-11       Impact factor: 2.943

8.  Thermal effects in the organocatalytic asymmetric Mannich reaction.

Authors:  Belén Rodríguez; Carsten Bolm
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

9.  An enantioselective biginelli reaction catalyzed by a simple chiral secondary amine and achiral brønsted acid by a dual-activation route.

Authors:  Junguo Xin; Lu Chang; Zongrui Hou; Deju Shang; Xiaohua Liu; Xiaoming Feng
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Selective compounds define Hsp90 as a major inhibitor of apoptosis in small-cell lung cancer.

Authors:  Anna Rodina; Maria Vilenchik; Kamalika Moulick; Julia Aguirre; Joungnam Kim; Anne Chiang; Julie Litz; Cristina C Clement; Yanlong Kang; Yuhong She; Nian Wu; Sara Felts; Peter Wipf; Joan Massague; Xuejun Jiang; Jeffrey L Brodsky; Geoffrey W Krystal; Gabriela Chiosis
Journal:  Nat Chem Biol       Date:  2007-07-01       Impact factor: 15.040

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  11 in total

Review 1.  Recent advances in C-heteroatom bond forming by asymmetric Michael addition.

Authors:  Majid M Heravi; Parvin Hajiabbasi
Journal:  Mol Divers       Date:  2013-12-31       Impact factor: 2.943

Review 2.  Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles.

Authors:  Majid M Heravi; Mansoureh Daraie; Vahideh Zadsirjan
Journal:  Mol Divers       Date:  2015-04-12       Impact factor: 2.943

Review 3.  Current progress in asymmetric Biginelli reaction: an update.

Authors:  Majid M Heravi; Razieh Moradi; Leyla Mohammadkhani; Borzou Moradi
Journal:  Mol Divers       Date:  2018-06-23       Impact factor: 2.943

Review 4.  Negishi coupling: an easy progress for C-C bond construction in total synthesis.

Authors:  Majid M Heravi; Elaheh Hashemi; Niousha Nazari
Journal:  Mol Divers       Date:  2014-03-07       Impact factor: 2.943

Review 5.  Overview on magnetically recyclable ferrite nanoparticles: synthesis and their applications in coupling and multicomponent reactions.

Authors:  Runjhun Tandon; Nitin Tandon; Shripad M Patil
Journal:  RSC Adv       Date:  2021-09-01       Impact factor: 4.036

6.  A Brønsted acidic ionic liquid anchored to magnetite nanoparticles as a novel recoverable heterogeneous catalyst for the Biginelli reaction.

Authors:  Hourieh Sadat Oboudatian; Hossein Naeimi; Mohsen Moradian
Journal:  RSC Adv       Date:  2021-02-11       Impact factor: 3.361

Review 7.  Samarium(ii) iodide-mediated reactions applied to natural product total synthesis.

Authors:  Majid M Heravi; Azadeh Nazari
Journal:  RSC Adv       Date:  2022-03-30       Impact factor: 3.361

8.  Efficient synthesis of dihydropyrimidinones via a three-component Biginelli-type reaction of urea, alkylaldehyde and arylaldehyde.

Authors:  Haijun Qu; Xuejian Li; Fan Mo; Xufeng Lin
Journal:  Beilstein J Org Chem       Date:  2013-12-11       Impact factor: 2.883

Review 9.  Multicomponent reactions in nucleoside chemistry.

Authors:  Mariola Koszytkowska-Stawińska; Włodzimierz Buchowicz
Journal:  Beilstein J Org Chem       Date:  2014-07-29       Impact factor: 2.883

10.  Sulfamic acid pyromellitic diamide-functionalized MCM-41 as a multifunctional hybrid catalyst for melting-assisted solvent-free synthesis of bioactive 3,4-dihydropyrimidin-2-(1H)-ones.

Authors:  Ehsan Valiey; Mohammad G Dekamin; Zahra Alirezvani
Journal:  Sci Rep       Date:  2021-05-27       Impact factor: 4.379

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