scholarly journals Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

2017 ◽  
Vol 13 ◽  
pp. 1396-1406 ◽  
Author(s):  
Roman A Irgashev ◽  
Nikita A Kazin ◽  
Gennady L Rusinov ◽  
Valery N Charushin

A new general approach to double nitration of 6,12-di(hetero)aryl-substituted and 6,12-unsubstituted 5,11-dialkyl-5,11-dihydroindolo[3,2-b]carbazoles by acetyl nitrate has been developed to obtain their 2,8-dinitro and 6,12-dinitro derivatives, respectively. A formation of mono-nitro derivatives (at C-2 or C-6) from the same indolo[3,2-b]carbazoles has also been observed in several cases. Reduction of 2-nitro and 2,8-dinitro derivatives with zinc powder and hydrochloric acid has afforded 2-amino- and 2,8-diamino-substituted indolo[3,2-b]carbazoles, while reduction of 6,12-dinitro derivatives under similar reaction conditions has been accompanied by denitrohydrogenation of the latter compounds into 6,12-unsubstituted indolo[3,2-b]carbazoles. Formylation of 6,12-dinitro derivatives has proved to occur only at C-2, while bromination of these compounds has taken place at both C-2 and C-8 of indolo[3,2-b]carbazole scaffold. Moreover, 6,12-dinitro-substituted indolo[3,2-b]carbazoles have been modified by the reactions with S- and N-nucleophiles. Notably, the treatment of 6,12-dinitro compounds with potassium thiolates has resulted in the displacement of both nitro groups, unlike potassium salts of indole or carbazole, which have caused substitution of only one nitro group.

2008 ◽  
Vol 5 (s2) ◽  
pp. 1087-1097 ◽  
Author(s):  
Afaf Abul Khier ◽  
Magda M. Elhenawee ◽  
Manal S. Elmasry

A simple spectrophorometric method for the determination of secnidazole, niclosamide, nifuroxazide and sulphasalzine is described. The method is based on reduction of the nitro group present in secnidazole and niclosamide molecule using zinc powder and dilute hydrochloric acid followed by reaction with fast red B salt in presence of ammonium chloride and sodium hydroxide, while in case of nifuroxazide and sulphasalazine the reaction takes place directly without any prior reduction between the phenolic group present in each drug and fast red B salt in presence of sodium hydroxide. Beer's law is valid in the concentration ranges 2.5-15, 1.25-10, 2.5-15, and 2.5-13.75 μg.mL-1for secnidazole, niclosamide, nifuroxazide and sulphasalazine respectively. The proposed method is applied successfully for the estimation of the mentioned drugs either in pure form or in their pharmaceutical formulations.


1987 ◽  
Vol 52 (10) ◽  
pp. 2482-2491 ◽  
Author(s):  
Ján Urban ◽  
Petr Kuzmič ◽  
David Šaman ◽  
Milan Souček

Anaerobic photolysis of dimethoxynitrobiphenyls IIIa-VIa in aqueous alkaline tert-butanol gave products of nucleophilic photosubstitution of methoxyl by hydroxide anion, while the dimethoxybiphenyls Ia and IIa were found unreactive. Regioselectivity of the reaction was examined in view of a possible “extended meta activation” by the nitro group. The most reactive substrate IIIa gives both C-3 and C-4 substitution products with an unsubstantial preference for the latter, which opposes the “extended meta selectivity” rule. All of the other compounds obey the rule, and 3,4-dimethoxy-3'-nitrobiphenyl (IVa) even displayed absolute selectivity by yielding C-3 substituted compound as the only product. 2,5-Dimethoxy substituted compounds underwent photosubstitution which much lower quantum yields than their 3,4-substituted counterparts, most probably due to some steric hindrance of conjugation. Similarly, 3-nitro-substituted biphenyls exhibited much lower overall reactivity than 4-nitro derivatives.


1973 ◽  
Vol 51 (6) ◽  
pp. 974-977 ◽  
Author(s):  
Malcolm B. Perry ◽  
Virginia Daoust

5-Deoxy-D-lyxose underwent base-catalyzed addition with nitromethane to give a mixture of 1,6-dideoxy-1-nitro-D-galactitol and 1,6-dideoxy-1-nitro-D-talitol (ca. 2:1). Acetylation of the crystalline 1,6-dideoxy-1-nitro-D-galactitol gave 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1-nitro-D-galactitol which on treatment with methanolic ammonia afforded 2-acetamido-1,2,6-trideoxy-1-nitro-D-talitol and 2-acetamido-1,2,6-trideoxy-1-nitro-D-galactitol (ca. 3:1) which under the modified Nef reaction conditions gave 2-acetamido-2,6-dideoxy-D-talose and 2-acetamido-2,6-dideoxy-D-galactose respectively. The glycoses were converted to 2-amino-2,6-dideoxy-D-talose hydrochloride and 2-amino-2,6-dideoxy-D-galactose hydrochloride on hydrolysis with hydrochloric acid.A similar reaction sequence applied to 5-deoxy-L-lyxose afforded the L-enantiomorphic intermediates, and gave 2-amino-2,6-dideoxy-L-talose hydrochloride and 2-amino-2,6-dideoxy-L-galactose hydrochloride as final products.


2019 ◽  
Vol 60 (3) ◽  
pp. 276-283 ◽  
Author(s):  
Rana Chatterjee ◽  
Satyajit Samanta ◽  
Anindita Mukherjee ◽  
Sougata Santra ◽  
Grigory V. Zyryanov ◽  
...  

1972 ◽  
Vol 50 (20) ◽  
pp. 3367-3372 ◽  
Author(s):  
A. Fischer ◽  
D. R. A. Leonard

Reaction of 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene with nitric acid in acetic anhydride gives two stereoisomeric 4-acetoxy-6a-nitro-3-oxo-1,2,3,4,6a,7,8,9,10,10a-decahydrocyclohepta[de]-naphthalenes as well as the expected nitro substitution products. Formation of these adducts from a substrate containing a meta-directing deactivating substituent shows that the 1,4-addition reaction of acetyl nitrate is more general than previously suspected. 1,4-Acetyl nitrate adducts are also formed from tetralin, benzsuberane, 5,6,7,8-tetrahydrocyclohepta[fg]acenaphthene, and 1,2,3,4,7,8,9,10-octahydrodicyclohepta[de,ij]naphthalene. Decomposition of the last two adducts gives in each case a product with the nitro group substituted into the alicyclic ring.


Crystals ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 389
Author(s):  
Varvara V. Avdeeva ◽  
Grigoriy A. Buzanov ◽  
Elena A. Malinina ◽  
Nikolay T. Kuznetsov ◽  
Anna V. Vologzhanina

A series of complexation reactions of silver(I) and copper(I) in the presence of a polyhedral weakly coordinating [B10Cl10]2− anion has been carried out. The effect of the solvent and the presence of Ph3P on the composition and structure of the reaction product were studied. Eight novel complexes were obtained and characterized by 11B Nuclear magnetic resonance, Infra-Red, and Raman spectroscopies as well as powder and single-crystal X-ray diffraction techniques. The [B10Cl10]2− anion demonstrated weaker coordinating ability towards coinage metals than [B10H10]2− at similar reaction conditions. The [B10Cl10]2− anion remains unreacted in the copper(I) complexation reaction, while in the absence of competing ligands, we obtained the first complexes containing decachloro-closo-decaborate anion directly coordinated by the metal atom. The bonding between metal atoms and the boron cluster anions was studied using the atomic Hirshfeld surfaces. Besides edge and face coordination of the polyhedral anion, this method allowed us to reveal the Ag–Ag bond in crystal of {Ag2(DMF)2[B10Cl10]}n, the presence of which was additionally supported by the Raman spectroscopy data.


1982 ◽  
Vol 37 (10) ◽  
pp. 1274-1278 ◽  
Author(s):  
Werner Roll ◽  
Ernst Otto Fischer ◽  
Dietmar Neugebauer ◽  
Ulrich Schubert

The reaction of trans-bromotetracarbonyl(phenylcarbyne)chromium (1) with lithium phenylselenolate and subsequent protonation with aqueous hydrochloric acid leads to (CO)5Cr[Se2(C6H5)2] (3) and (CO)4Cr(μ-SeC6H5)2Cr(CO)4 (4). From 1 and lithium 4-methylphenylthiolate (CO)5CrC(C6H5)SC6H4CH3 (5) and (CO)5CrS(C2H5)(4-CH3C6H4) (6) are obtained, if triethyloxonium tetrafluoroborate is used instead of hydrochloric acid. The analoguous reaction of 1 with lithium phenylselenolate yields the seleno ether complex (7). Reaction conditions, properties, spectroscopic data and the results of an X-ray structure determination of the binuclear complex (4) are reported.


1967 ◽  
Vol 20 (2) ◽  
pp. 359 ◽  
Author(s):  
JFK Wilshire

The reaction of selenium dioxide with indole in benzene gives 3,3?- diindolyl selenide. In separate experiments but with similar reaction conditions, 2-methyl-indole gave complex mixtures from which either 3,3?-di(2-methylindolyl) diselenide or the corresponding triselenide was isolated in low yield. 1,2-Dimethylindole gave 3,3?-di(1,2- dimethylindolyl) triselenide, also in low yield.


2018 ◽  
Vol 5 (1) ◽  
pp. 90-99 ◽  
Author(s):  
Haifeng Gao ◽  
Zhiwei Yao ◽  
Yan Shi ◽  
Renren Jia ◽  
Feixue Liang ◽  
...  

The catalytic stability of monometallic β-Mo2C/CNTs was found to be superior to that of bimetallic Ni/β-Mo2C under similar reaction conditions.


2008 ◽  
Vol 27 (2) ◽  
pp. 117 ◽  
Author(s):  
Shahriare Ghammamy ◽  
Mohammad Kazem Mohammadi ◽  
Ali Hassani Joshaghani

Triethylammonium halochromates, (C2H5)3NCrO3X, TEAXC (X = Cl, F) are easily synthesized by the reaction of triethylamine with a solution of chromium(VI) oxide in 6M hydrochloric acid, or a solution of chromium(VI) oxide in 40% hydrofluoric acid. These reagents are easily supported on common silica gel and can be used as heterogeneous oxidants. Triethylammonium halochromate(VI) is a versatile reagent for the effective and selective oxidation of organic substrates. Various aliphatic (cyclic and acyclic) and aromatic thiols are converted into the corresponding disulfides by treatment with triethylammonium fluorochromate(VI), (TEACC) or triethylammonium chlorochromate(VI), (TEAFC) supported on silica gel, in excellent yields and under mild reaction conditions.


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