Literature DB >> 33534024

Friedel-Crafts synthesis of bis(trifluoromethylated)-4-aryl-3,4-dihydroquinazolines, bis(trifluoromethylated)-3,4-dihydroquinazoline-4-ols and trifluoromethyl arylketoimines using N-aryltrifluoroacetimidoyl chlorides and benzene derivatives.

Elham Kazemi1, Ali Darehkordi2, Alireza Abbasi3.   

Abstract

A simple and straightforward approach to access biologically important N-heterocycles, namely bis(trifluoromethylated)-4-aryl-3,4-dihydroquinazolines, bis(trifluoromethylated)-3,4-dihydroquinazoline-4-ols and trifluoromethyl arylketoimines, as a group of important frameworks or initial substance from N-aryltrifluoroacetimidoyl chlorides with benzene derivatives via Friedel-Crafts reaction has been described. This novel strategy provides synthesis of trifluoromethylated dihydroquinazolines and trifluoromethyl arylketoimines in good to excellent yields.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG part of Springer Nature.

Entities:  

Keywords:  Bis(trifluoromethylated)-3,4-dihydroquinazoline-4-ols; Bis(trifluoromethylated)-4-aryl-3,4-dihydroquinazolines; Trifluoromethyl arylketoimines and N-aryltrifluoroacetimidoyl chlorides

Mesh:

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Year:  2021        PMID: 33534024     DOI: 10.1007/s11030-021-10189-4

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


  17 in total

1.  Discovery of potent T-type calcium channel blocker.

Authors:  Han Na Seo; Ja Youn Choi; Yun Jeong Choe; Yoonjee Kim; Hyewhon Rhim; So Ha Lee; Jungahn Kim; Dong Jun Joo; Jae Yeol Lee
Journal:  Bioorg Med Chem Lett       Date:  2007-09-01       Impact factor: 2.823

Review 2.  Synthetic methods for compounds having CF3-S units on carbon by trifluoromethylation, trifluoromethylthiolation, triflylation, and related reactions.

Authors:  Xiu-Hua Xu; Kohei Matsuzaki; Norio Shibata
Journal:  Chem Rev       Date:  2014-08-14       Impact factor: 60.622

3.  Synthesis and biological evaluation of novel T-type calcium channel blockers.

Authors:  Ja Youn Choi; Han Na Seo; Min Joo Lee; Seong Jun Park; Sung Jun Park; Ji Young Jeon; Joo Hi Kang; Ae Nim Pae; Hyewhon Rhim; Jae Yeol Lee
Journal:  Bioorg Med Chem Lett       Date:  2006-10-12       Impact factor: 2.823

4.  The palladium-catalyzed trifluoromethylation of aryl chlorides.

Authors:  Eun Jin Cho; Todd D Senecal; Tom Kinzel; Yong Zhang; Donald A Watson; Stephen L Buchwald
Journal:  Science       Date:  2010-06-25       Impact factor: 47.728

5.  3,4-Dihydroquinazoline derivatives as novel selective T-type Ca2+ channel blockers.

Authors:  Yong Sup Lee; Bum Hoon Lee; Seong Jun Park; Soon Bang Kang; Hyewhon Rhim; Jin-Yong Park; Jung-Ha Lee; Seong-Woo Jeong; Jae Yeol Lee
Journal:  Bioorg Med Chem Lett       Date:  2004-07-05       Impact factor: 2.823

Review 6.  Fluorine in medicinal chemistry.

Authors:  Sophie Purser; Peter R Moore; Steve Swallow; Véronique Gouverneur
Journal:  Chem Soc Rev       Date:  2007-12-13       Impact factor: 54.564

7.  2-Amino-3,4-dihydroquinazolines as inhibitors of BACE-1 (beta-site APP cleaving enzyme): Use of structure based design to convert a micromolar hit into a nanomolar lead.

Authors:  Ellen W Baxter; Kelly A Conway; Ludo Kennis; François Bischoff; Marc H Mercken; Hans L De Winter; Charles H Reynolds; Brett A Tounge; Chi Luo; Malcolm K Scott; Yifang Huang; Mirielle Braeken; Serge M A Pieters; Didier J C Berthelot; Stefan Masure; Wouter D Bruinzeel; Alfonzo D Jordan; Michael H Parker; Robert E Boyd; Junya Qu; Richard S Alexander; Douglas E Brenneman; Allen B Reitz
Journal:  J Med Chem       Date:  2007-08-08       Impact factor: 7.446

8.  Alpha-trifluoromethylated carbanion synthons.

Authors:  Kenji Uneyama; Toshimasa Katagiri; Hideki Amii
Journal:  Acc Chem Res       Date:  2008-06-14       Impact factor: 22.384

Review 9.  Quinoline, quinazoline and acridone alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2003-10       Impact factor: 13.423

10.  Dihydroquinazolines as a novel class of Trypanosoma brucei trypanothione reductase inhibitors: discovery, synthesis, and characterization of their binding mode by protein crystallography.

Authors:  Stephen Patterson; Magnus S Alphey; Deuan C Jones; Emma J Shanks; Ian P Street; Julie A Frearson; Paul G Wyatt; Ian H Gilbert; Alan H Fairlamb
Journal:  J Med Chem       Date:  2011-09-01       Impact factor: 7.446

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