scholarly journals A convergent strategy towards febrifugine and related compounds

2018 ◽  
Vol 16 (22) ◽  
pp. 4159-4169 ◽  
Author(s):  
T. M. M. Maiden ◽  
N. Mbelesi ◽  
P. A. Procopiou ◽  
S. Swanson ◽  
J. P. A. Harrity

We report a modular five step synthetic route to the febrifugines that employs 2-(chloromethyl)allyl-trimethylsilane as a conjunctive reagent for the coupling of the piperidine and quinazolinone groups.

Tetrahedron ◽  
1997 ◽  
Vol 53 (5) ◽  
pp. 1593-1606 ◽  
Author(s):  
Hideharu Suzuki ◽  
Chiemie Iwata(nee Miyaga) ◽  
Katsumi Sakurai ◽  
Kazuhiko Tokumoto ◽  
Hiroko Takahashi ◽  
...  

2016 ◽  
Vol 72 (7) ◽  
pp. 549-554 ◽  
Author(s):  
Lina M. Acosta Quintero ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell

Compounds containing the tricyclic dibenzo[b,e]azepine system have potential activity in the treatment of a number of diseases. Continuing with our studies on the synthesis of new small and potentially bioactive molecules, a synthetic route, involving acid-catalysed intramolecular Friedel–Crafts cyclization, to the readily separable diastereoisomers of 11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxamide, a potentially useful precursor in the synthesis of analogues of some anti-allergenic, antidepressant and antihistaminic drugs currently in use, has been developed starting from 2-allylphenylamine and methyl 2-bromo-2-phenylacetate and proceedingviaracemic methyl 2-[(2-allylphenyl)amino]-2-phenylacetate (A) and racemic 2-[(2-allylphenyl)amino]-2-phenylacetamide (B), to give the two diastereoisomers (I) and (II), C17H18N2O. Isomers (I) and (II), and their precursors (A) and (B), have all been fully characterized spectroscopically. Structure analysis of the minor isomer (I) shows that it has the (6RS,11RS) configuration, and that the azepine ring adopts a conformation intermediate between the boat and twist-boat forms, with the carboxamide and ethyl substituents both occupying quasi-equatorial sites. The molecules of (I) are linked by a combination of N—H...O, N—H...π(arene) and C—H...π(arene) hydrogen bonds to form complex sheets. Comparisons are made with the structures of some related compounds.


Heterocycles ◽  
1996 ◽  
Vol 43 (1) ◽  
pp. 101 ◽  
Author(s):  
Masao Tsukayama ◽  
Akihiro Sogawa ◽  
Hiroshi Nozaki ◽  
Mitsuru Nakayama

1982 ◽  
Vol 60 (5) ◽  
pp. 572-573 ◽  
Author(s):  
George M. Strunz ◽  
G. Sankar Lal

A convenient "one-pot" modification of a conventional synthetic route affords 2-hydroxy-3-methylcyclopent-2-en-1-one and related compounds in high overall yields.


Synthesis ◽  
1993 ◽  
Vol 1993 (08) ◽  
pp. 783-785 ◽  
Author(s):  
Ricardo Bossio ◽  
Stefano Marcaccini ◽  
Roberto Pepino ◽  
Tomás Torroba

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