- On the reaction of 3-bromo-2-nitrobenzo[b]thiophene with some ortho-substituted anilines: An analysis of the products of reaction and of their NMR and MS properties
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The title reaction, carried out in DMF in the presence of triethylamine or potassium carbonate, has furnished the 'expected' 3-amino-2-nitrobenzo[b]thiophenes 2o together with the 'unexpected' 2-amino-3-nitrobenzo[b]thiophenes 3o, thus recalling the situation observed with other weak nucleophiles in the presence of non-nucleophilic bases. The effects (electronic as well as steric) of the ortho-substituent (OH, NH 2, OMe, Me, Et, F, Cl and Br) on the course of the reaction have been investigated, determining their influence on yields and product ratios (2o/3o). An analysis of 13C NMR and MS spectra of 2o and 3o has been carried out. Ab initio computations on 2of, 2oi, 3of and 3oi at DFT level have furnished informations on their geometry and stability in the gas phase, thus allowing to assign a role to their stability on the course of the reaction as well as on some EI-MS results.
- Cosimelli, Barbara,Lamartina, Liliana,Lanza, Camilla Zaira,Spinelli, Domenico,Spisani, Raffaella,Vegna, Federica
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- Synthesis and pharmacological properties of 2-nitro-3-substituted-amino benzo[b]thiophenes and their 5-chloro derivatives
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This paper reports the synthesis and the pharmacological evaluation of some 2-nitro-3-N-phenylamino-benzo[b]-thiophenes and 5-chloro derivatives of the most active of these compounds; in addition, some 5-chloro derivatives of 2-nitro-3-alkylen- or phenylen-diamino-benzo[b]thiophenes previously synthesized were prepared. These compounds were screened for analgesic, antiexudative and antiinflammatory activities related to phenylbutazone. Nitration of 5-chloro-3-bromobenzo[b]thiophene was also studied.
- Guerrera,Salerno,Sarva,Siracusa,Lamartina,Caruso,Cutuli
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p. 1149 - 1160
(2007/10/02)
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