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| Utilization of bromine azide to access vicinal-azidobromides from arylidene malononitrile |
| Hanan A. Solimana, Tamer K. Khatabb, Farouk M. E. Abdel-Megeida |
a Photochemistry Department, National Research Centre, Dokki 12622, Egypt;
b Organometallic and Organometalloid Chemistry Department, National Research Centre, Dokki 12622, Egypt |
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Abstract An efficient and facile approach for tetrachlorosilane as an in situ mediated transformation via a one-pot, synthesis of vicinal bromoazides through the generation of BrN3 from azidochlorosilane and N-bromosuccinimide in acetonitrile as solvent at ambient temperature is achieved. This catalytic process represents a highly regioselective and high yielding method for the synthesis of 1,2-bromoazides. Thiamine pyrophosphate (TPP) riboswitches regulate essential genes in bacteria by changing conformation upon binding intracellular TPP. Molecular docking studies are conducted to understand the orientation and the interaction of each synthesized molecules with TPP riboswitches. 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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Received: 24 January 2016
Published: 24 March 2016
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| [1] |
S.H. Bauer, An electron diffraction investigation of the structure of difluorodiazine, J. Am. Chem. Soc. 69(1947) 3104-3108.
|
| [2] |
K. Dehnicke, Reactions of halogen azides, Angew. Chem. Int. Ed. Engl. 6(1967) 240-246.
|
| [3] |
(a) A. Hassner, F. Boerwinkle, Ionic and free-radical addition of bromine azide to olefins, J. Am. Chem. Soc. 90(1968) 216-218; (b) F. Boerwinkle, A. Hassner, Solvent participation in additions to olefin, Tetrahedron Lett. 9(1968) 39213924; (c) A. Hassner, F. Boerwinkle, Free radical vs ionic additions of halogen azides to olefins, Tetrahedron Lett. 10(1969) 3309-3319.
|
| [4] |
A. Hassner, J.S. Teeter, Stereochemistry. LIV. Phenyl migration in pseudo halogen additions to 3,3,3-triphenylpropene, J. Org. Chem. 35(1970) 3397-3401.
|
| [5] |
A. Hassner, Regiospecific and stereospecific introduction of azide functions into organic molecules, Acc. Chem. Res. 4(1971) 9-16.
|
| [6] |
G. L'Abbe, A. Hassner, Synthesis of a-azidovinyl ketones from the iodine azide adducts of a,b-unsaturated ketones, J. Org. Chem. 36(1971) 258-260.
|
| [7] |
G. L'Abbé, A. Hassner, Neue methoden zur darstellung von vinylaziden, Angew. Chem. Int. Ed. Engl. 10(1971) 98-104.
|
| [8] |
A. Hassner, J. Keogh, Addition of halogen azides to non-cyclic conjugated dienes, Tetrahedron Lett. 16(1975) 1575-1578.
|
| [9] |
K. Ponsold, M. Wunderwald, Gekoppelte additionsreaktionen an 14,15-ungesättigten androstanen einfluß des positiven halogens auf die regioselektivität, J. Prakt. Chem. (Leipzig) 325(1983) 123-132.
|
| [10] |
R.W. Nagorski, R.S. Brown, Electrophilic addition of bromine to olefins in the presence of nucleophilic trapping anions. Implications for the lifetimes of bromonium ion intermediates produced from electrophilic bromination of olefins in methanol, J. Am. Chem. Soc. 114(1992) 7773-7779.
|
| [11] |
D. Van Ende, A. Krief, A new reagent for stereospecific synthesis of aziridines from olefins, Angew. Chem. Int. Ed. Engl. 13(1974) 279-280.
|
| [12] |
J.N. Denis, A. Krief, New synthetic route to 9,10-imino-phenanthrene, Tetrahedron 35(1979) 2901-2903.
|
| [13] |
I.C. Chiu, H. Kohn, Syntheses and reactivity of trans-6-azabicyclo[3.1.0] hexan-2-ol derivatives and indanol[1,2-b]aziridine. Structural analogs of mitomycin C, J. Org. Chem. 48(1983) 2857-2866.
|
| [14] |
N.M. Nguy, I.C. Chiu, H. Kohn, Synthesis and reactivity of 6- and 7-methoxyindano[1,2-b]aziridines, J. Org. Chem. 52(1987) 1649-1655.
|
| [15] |
W. Lange, W. Tueckmantel, Synthesis and reactions of oligomethylene-clamped 1 H-azepines and benzene imines. Their valence tautomeric equilibrium and nitrogen stereochemistry, Chem. Ber. 122(1989) 1765-1976.
|
| [16] |
D.A. Devalankar, A. Sudalai, A concise synthesis of (+)-deoxoprosophylline via Co(Ⅲ)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides, Tetrahedron Lett. 53(2012) 3213-3215.
|
| [17] |
I. Saikia, P.C. Phukan, Catalyst-free vicinal bromoazidation of olefins using TMSN3 and NBS, C.R. Chim. 15(2012) 688-692.
|
| [18] |
S. Hajra, D. Sinha, M. Bhowmick, Metal triflate catalyzed highly regio- and stereoselective 1,2-bromoazidation of alkenes using NBS and TMSN3 as the bromine and azide sources, Tetrahedron Lett. 47(2006) 7017-7019.
|
| [19] |
S. Hajra, D. Sinha, M. Bhowmick, Metal triflate catalyzed reactions of alkenes, NBS, nitriles, and TMSN3:synthesis of 1,5-disubstituted tetrazoles, J. Org. Chem. 72(2007) 1852-1855.
|
| [20] |
S. Hajra, M. Bhowmick, D. Sinha, Highly regio- and stereoselective asymmetric bromoazidation of chiral a,b-unsaturated carboxylic acid derivatives:scope and limitations, J. Org. Chem. 71(2006) 9237-9240.
|
| [21] |
I. Saikia, P. Phukan, Facile generation of vicinal bromoazides from olefins using TMSN3 and TsNBr2 without any catalyst, Tetrahedron Lett. 50(2009) 5083-5087.
|
| [22] |
A. Kumar, M.S. Rao, V. Mehta, A simple and efficient bromoazidation of alkenes using PTT and TMSN3 in ionic liquid, Indian, J. Chem., Sect. B:Org. Chem. Incl. Med. Chem. 50B (2011) 1123-1127.
|
| [23] |
A. Hassner, F.W. Fowler, General synthesis of vinyl azides from olefins. Stereochemistry of elimination from b-iodo azides, J. Org. Chem. 33(1968) 2686-2691.
|
| [24] |
H.H. Wasserman, R.K. Brunner, J.D. Buynak, et al., Total synthesis of (±)-Omethylorantine, J. Am. Chem. Soc. 107(1985) 519-521.
|
| [25] |
(a) S. Ranganathan, D. Ranganathan, A.K. Mehrotra, The "Hassner-Ritter" reaction in iodine azide additions to pinenes with solvent participation, Tetrahedron Lett. 14(1973) 2265-2266; (b) S.N. Moorthy, D. Devaprabakara, Addition of iodine azide to C-9 and C-10 medium-ring dienes, Tetrahedron Lett. 16(1975) 257-260.
|
| [26] |
(a) D. Van Ende, A. Krief, A highly potent reagent for regioselective and stereospecific synthesis of polyenes bearing terminal aziridine groups, Angew. Chem. Int. Ed. Engl. 13(1974) 279-280; (b) J.N. Denis, A. Krief, New synthetic route to 9,10-imino-phenanthrene 1, Tetrahedron 35(1979) 2901-2903.
|
| [27] |
S. Rossi, M. Benaglia, A. Genoni, Organic reactions mediated by tetrachlorosilane, Tetrahedron 70(2014) 2065-2080.
|
|
|
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