Literature DB >> 30953294

Facile, efficient and one-pot access to diverse new functionalized aminoalkyl and amidoalkyl naphthol scaffolds via green multicomponent reaction using triethylammonium hydrogen sulfate ([Et3NH][HSO4]) as an acidic ionic liquid under solvent-free conditions.

Elahe Hadadianpour1, Behjat Pouramiri2.   

Abstract

An efficient, clean and one-pot multicomponent synthesis of divers kind of new functionalized aminoalkyl naphthol and amidoalkyl naphthol derivatives via tandem condensation reaction of 2-naphthol, aromatic aldehydes and 5-methyl-1,3,4-thiadiazol-2-amine/5-aryl-1,3,4-thiadiazol-2-amines urea/acetamide under solvent-free conditions is reported. Following this protocol, it was possible to synthesize novel 1-(((5-methyl-1,3,4-thiadiazol-2-yl)amino)(aryl)methyl)naphthalen-2-ol, 1-(aryl((5-aryl-1,3,4-thiadiazol-2-yl)amino)methyl)naphthalen-2-ol and amidoalkyl naphthol derivatives. This protocol includes some salient features, such as the use of triethylammonium hydrogen sulfate ([Et3NH][HSO4]) ionic liquid as a green, clean and reusable catalyst, no column chromatographic separation, high atom economy, good yields, low cost and finally no need for a complex procedure.

Entities:  

Keywords:  1-Aminoalkyl-2-naphthol; Green synthesis; Multicomponent reaction (MCRs); No column chromatography; Solvent-free conditions

Year:  2019        PMID: 30953294     DOI: 10.1007/s11030-019-09945-4

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


  29 in total

1.  Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity.

Authors:  F Clerici; D Pocar; M Guido; A Loche; V Perlini; M Brufani
Journal:  J Med Chem       Date:  2001-03-15       Impact factor: 7.446

2.  Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists.

Authors:  Tomoaki Hasui; Nobuyuki Matsunaga; Taiichi Ora; Norio Ohyabu; Nobuhiro Nishigaki; Yoshimi Imura; Yumiko Igata; Hideki Matsui; Takashi Motoyaji; Toshimasa Tanaka; Noriyuki Habuka; Satoshi Sogabe; Midori Ono; Christopher S Siedem; Tony P Tang; Cassandra Gauthier; Lisa A De Meese; Steven A Boyd; Shoji Fukumoto
Journal:  J Med Chem       Date:  2011-11-29       Impact factor: 7.446

3.  Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides.

Authors:  Xing-Hai Liu; Yan-Xia Shi; Yi Ma; Chuan-Yu Zhang; Wei-Li Dong; Li Pan; Bao-Lei Wang; Bao-Ju Li; Zheng-Ming Li
Journal:  Eur J Med Chem       Date:  2009-01-22       Impact factor: 6.514

4.  Green chemistry: principles and practice.

Authors:  Paul Anastas; Nicolas Eghbali
Journal:  Chem Soc Rev       Date:  2009-11-20       Impact factor: 54.564

5.  Bortezomib or high-dose dexamethasone for relapsed multiple myeloma.

Authors:  Paul G Richardson; Pieter Sonneveld; Michael W Schuster; David Irwin; Edward A Stadtmauer; Thierry Facon; Jean-Luc Harousseau; Dina Ben-Yehuda; Sagar Lonial; Hartmut Goldschmidt; Donna Reece; Jesus F San-Miguel; Joan Bladé; Mario Boccadoro; Jamie Cavenagh; William S Dalton; Anthony L Boral; Dixie L Esseltine; Jane B Porter; David Schenkein; Kenneth C Anderson
Journal:  N Engl J Med       Date:  2005-06-16       Impact factor: 91.245

6.  Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound.

Authors:  Wojciech Rzeski; Joanna Matysiak; Martyna Kandefer-Szerszeń
Journal:  Bioorg Med Chem       Date:  2007-02-22       Impact factor: 3.641

Review 7.  Recent advances in isocyanide-based multicomponent chemistry.

Authors:  Alexander Dömling
Journal:  Curr Opin Chem Biol       Date:  2002-06       Impact factor: 8.822

8.  Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives.

Authors:  Cai-Jun Chen; Bao-An Song; Song Yang; Guang-Fang Xu; Pinaki S Bhadury; Lin-Hong Jin; De-Yu Hu; Qian-Zhu Li; Fang Liu; Wei Xue; Ping Lu; Zhuo Chen
Journal:  Bioorg Med Chem       Date:  2007-04-10       Impact factor: 3.641

9.  Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents.

Authors:  D A Ibrahim
Journal:  Eur J Med Chem       Date:  2009-01-19       Impact factor: 6.514

10.  CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones.

Authors:  Varsha Jatav; Pradeep Mishra; Sushil Kashaw; J P Stables
Journal:  Eur J Med Chem       Date:  2007-12-23       Impact factor: 6.514

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  1 in total

1.  Triethylammonium Hydrogen Sulfate [Et3NH][HSO4]-Catalyzed Rapid and Efficient Multicomponent Synthesis of Pyrido[2,3-d]pyrimidine and Pyrazolo[3,4-b]pyridine Hybrids.

Authors:  Chetan Jadhav; Amol Nipate; Asha Chate; Charansingh Gill
Journal:  ACS Omega       Date:  2021-07-02
  1 in total

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