Synthesis of a new phorbazole and its derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
David Young ◽  
Wendy Loughlin ◽  
I Wayan Muderawan

Phorbazoles are chlorinated marine alkaloids isolated from sea sponges and nudibranchs. In this work, a convenience synthetic method leading to a new phorbazole and its derivatives was developed. This synthesis of the novel phorbazole G and its derivatives has been Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole, phenol ring units and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives was developed. This synthesis of the synthetic phorbazole G and its derivatives has been achieved in seven steps in good overall yields of 26-52 %. It involved formation of the pyrrole oxazole skeleton followed by chlorination. The pyrrole oxazole skeleton was synthesized from pyrrole and substituted acetophenones, and the key step was cyclodehydration of the amides to give protected oxazoles, followed by hydrolysis. achieved in seven steps in good overall yields of 26.3 - 52.5 %. It involved formation of the pyrrole oxazole skeleton followed by chlorination. The pyrrole oxazole skeleton was synthesized from pyrrole and substituted acetophenones, and the key step was cyclodehydration of the amides to give protected oxazoles, followed by hydrolysis

1998 ◽  
Vol 51 (4) ◽  
pp. 293 ◽  
Author(s):  
Graham A. Bowmaker ◽  
Peter C. Junk ◽  
Aaron M. Lee ◽  
Brian W. Skelton ◽  
Allan H. White

Syntheses and room-temperature single-crystal X-ray studies are recorded for a variety of salts of cations derived from protonated 2,2′-bipyridine and 1,10-phenanthroline (bpyH+ and phenH+) with polyhalobismuthate(III) anions. ‘[(phenH)(phenH2)(H2O)2] [BiCl6]’ is triclinic, P-1, a 9·791(1), b 9·338(3), c 8·311(3) Å, α 73·46(3), β 69·71(2), γ 86·36(2)°, Z = 1; conventional R on |F| was 0·027 for No 4852 independent ‘observed’ (I > 3σ(I)) reflections. [BiCl6]3- is closely octahedral, accompanied by an interesting protonation/hydrogen-bonding array among the other moieties. The latter comment applies also to ‘[(phenH2)(H2O)][BiCl5](∞|∞)’, monoclinic, P2/c, a 8·388(1), b 12·004(1), c 17·146(3) Å, β 98·26(1)°, Z = 4, R 0·047 for No 2670, the anion array being a one-dimensional polymer with bridging chlorine atoms occupying cis sites in the pseudo-octahedral coordination sphere of the bismuth. [bpyH2]4 [Bi4Cl20] is monoclinic, P21/c, a 14·228(4), b 14·217(2), c 16·254(4) Å, β 110·14(2)°, Z = 2, R 0·045 for No 2777; in the novel centrosymmetric tetramer, the four bismuth atoms are bridged into a square array by four linearly coordinated halogen atoms at the centres of the edges, a pair of these lying cis in the pseudo-octahedral coordination sphere of each bismuth. [bpyH]3 [Bi2Cl9] is triclinic, P-1 a 19·288(7), b 14·251(3), c 7·644(3) Å, α 75·02(2), β 80·15(3), γ 72·76(2)°, Z = 2, R 0·072 for No 3600, the two pseudo-octahedrally coordinated bismuth atoms being bridged by three chlorine atoms on a mutual octahedral face, [Cl3Bi(µ-Cl)3BiCl3]3-. [phenH] [BiCl4](∞|∞),H2O is triclinic, space group P-1, a 12·119(7), b 10·169(6), c 7·247(4) Å, α 69·30(4), β 75·05(4), γ 77·92(5)°, Z = 2, R 0·035 for No 2348. The anion is a one-dimensional polymer, successive metal atoms being bridged by pairs of chlorine atoms lying cis in the pseudo-octahedral coordination sphere. [bpyH]4 [Bi2I10] is monoclinic, P21/n, a 13·426(4), b 14·396(6), c 14·539(5) Å, β 101·31(3)°, Z = 2, R 0·11 for No 1862; the anion is of the form [I4Bi(µ-I)2BiI4]4- with quasi-octahedral bismuth. [bpyH] [BiI4](∞|∞) is monoclinic, C2/c, a 12·442(5), b 18·41(2), c 7·714(2) Å, β 92·80(3)°, Z = 4, R 0·080 for No 850, with a polymeric one-dimensional anion comparable to that in [phenH] [BiCl4](∞|∞),H2O. The structure of the 2,6-dimethylpyridinium salt of [BiCl6]3- is also recorded, as its acetonitrile solvate; triclinic, P-1, a 15·025(2), b 10·357(3), c 9·964(1) Å, α 83·14(2), β 89·32(1), γ 86·61(2)°, Z = 2, R 0·046 for No 3601; there is also an isomorphous bromide, and also an isostoichiometric bromide modelled as monoclinic, Cm, a 18·128(6), b 10·348(2), c 10·241(2) Å, β 121·31(3)°, Z = 2, R 0·050 for No 1379. Bands in the far-infrared and Raman spectra due to the v(BiCl) modes are assigned in [(phenH)(phenH2)(H2O)2] [BiCl6] and [bpyH2]4 [Bi4Cl20], and are discussed in relation to the structures of the complexes.


1969 ◽  
Vol 15 (3) ◽  
pp. 309-312
Author(s):  
Manuel Rodríguez-Rebollo ◽  
Cándida González Vázquez

The herbicide, 4-(2, 4-dichlorophenoxy)butyric acid (4-(2, 4-DB)), inhibited growth and lysed cells of Halohacterium salinarium at a concentration of 0.21 mM, a concentration considerably less than required for inhibition by other herbicides. The effective group is the phenol ring linked to chlorine atoms.


Neophilology ◽  
2019 ◽  
pp. 349-356
Author(s):  
Ekaterina Alekseevna TUTATINA

We consider history of the book title and how its role in the book and its place in the book edition changed. It also addresses the problem of studying the title of a book in Russian and foreign practices from the point of view of its poetics and functions, both in close connection with the text of the work, and with the help of the “distant reading” method. It is also being reviewed some current trends in book naming in modern publishing practices, such as the extensive use of citation and allusion techniques, the desire to reduce the title to a few characters, as well as the use of the letters of the Latin alphabet. The problems of the connection between the title and the genre of the novel and the structure of the title are also described. Separately, the question of the responsibility of the editor when working with the title of the translated work is raised. With concrete examples the problems of choosing the title of a book in the process of editorial preparation were analyzed,as well as some errors that the editor may make, dwelling on one or another variant of the title. We use the analytical-synthetic method of research. At the end of the work there are the main conclusions from the study.


2010 ◽  
Vol 34 (8) ◽  
pp. S33-S33
Author(s):  
Wenchao Ou ◽  
Haifeng Chen ◽  
Yun Zhong ◽  
Benrong Liu ◽  
Keji Chen

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