Бромирование по CH-группе аминосодержащих гетероциклов
Бромирование по CH-группе аминосодержащих гетероциклов
Уважаемые коллеги, подскажите методики бромирования CH-группы гетероциклов содержащих в своей структуре аминную функцию.
Re: Бромирование по CH-группе аминосодержащих гетероциклов
Нарисуйте конкретные соединения
Сходу могу сказать что надо проацелировать аминогруппу 0,4 мл Br2 + 30 мл THF
Почитать можно здесь:
1. J Rebek Jr, S H Shaber, Y-K Shue, J-C Gehret, S Zimmerman, J Org Chem [JOCEAH], 49 (26), p. 5164, 1984
2. S W Heinzman, J R Grunwell, Tetrahedron Lett [TELEAY], 21, p. 4305, 1980
Сходу могу сказать что надо проацелировать аминогруппу 0,4 мл Br2 + 30 мл THF
Почитать можно здесь:
1. J Rebek Jr, S H Shaber, Y-K Shue, J-C Gehret, S Zimmerman, J Org Chem [JOCEAH], 49 (26), p. 5164, 1984
2. S W Heinzman, J R Grunwell, Tetrahedron Lett [TELEAY], 21, p. 4305, 1980
Reactant BRN 105785 pyridin-2-ylamine
Product BRN 108737 5-bromo-pyridin-2-ylamine
Reaction Details 1 of 8
Reaction Classification Preparation
Yield 92 percent Chromat. (BRN=108737)
Reagent 4DABCO*6HBr*4Br2/SiO2
Solvent CH2Cl2
Time 2 min
Temperature 20 C
Ref. 1 6583579; Journal; Heravi, Majid M.; Derikvand, Fatemeh; Ghassemzadeh, Mitra; SAJCDG; S. Afr. J. Chem.; EN; 59; 2006; 125 - 128.
Reaction Details 2 of 8
Reaction Classification Preparation
Yield 93 percent (BRN=108737)
Reagent hexamethylenetetramine-bromine complex
Solvent CH2Cl2
Temperature 20 C
Ref. 1 6572391; Journal; Heravi, Majid M.; Abdolhosseini, Nafiseh; Oskooie, Hossein A.; TELEAY; Tetrahedron Lett.; EN; 46; 51; 2005; 8959 - 8963.
Reaction Details 3 of 8
Reaction Classification Preparation
Yield 91 percent (BRN=108737)
Reagent 1-butyl-3-methylimidazolium tribromide
Time 5 min
Temperature -10 C
Ref. 1 6488040; Journal; Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo; SYNTBF; Synthesis; EN; 17; 2004; 2809 - 2812.
Reaction Details 4 of 8
Reaction Classification Preparation
Yield 93 percent (BRN=108737)
Reagent NBS
Solvent acetonitrile
Time 17 hour(s)
Temperature 20 C
Ref. 1 6311255; Journal; Canibano, Victoria; Rodriguez, Justo F.; Santos, Mercedes; Sanz-Tejedor, M. Ascension; Carreno, M. Carmen; Gonzalez, Gema; Garcia-Ruano, Jose L.; SYNTBF; Synthesis; EN; 14; 2001; 2175 - 2179.
Reaction Details 5 of 8
Reaction Classification Preparation
Yield 86 percent (BRN=108737)
Reagent bromine
Solvent acetic acid
Time 2 hour(s)
Temperature 20 C
Ref. 1 5632546; Journal; Saidova, F. M.; Binchkauskas, V. Sh.; Khorev, S. G.; Enikeev, E. Ya.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); EN; 17; 2; 1981; 353-357; ZORKAE; Zh. Org. Khim.; RU; 17; 2; 1981; 413-417.
Reaction Details 6 of 8
Reaction Classification Preparation
Yield 53 percent (BRN=108737)
Reagent 3-bromo-6-chloroimidazo<1,2-b>pyridazine hydrobromide-bromine complex
Time 2 hour(s)
Ref. 1 5571197; Journal; Stanovnik, Branko; Tisler, Miha; Drnovsek, Iztok; SYNTBF; Synthesis; EN; 12; 1981; 987-989.
Reaction Details 7 of 8
Reaction Classification Preparation
Reagent diluted aqueous H2SO4
bromine
Ref. 1 1074318; Journal; Bradlow; Vanderwerf; JOCEAH; J. Org. Chem.; 16; 1951; 73, 79.
Reaction Details 8 of 8
Reaction Classification Preparation
Reagent acetic acid
acetic acid anhydride
bromine
Temperature 55 C
Other Conditions Erwaermen des Reaktionsprodukts mit wss.-aethanol. HCl
Ref. 1 987388; Journal; Caldwell et al.; JACSAT; J. Am. Chem. Soc.; 66; 1944; 1479, 1482.
Product BRN 108737 5-bromo-pyridin-2-ylamine
Reaction Details 1 of 8
Reaction Classification Preparation
Yield 92 percent Chromat. (BRN=108737)
Reagent 4DABCO*6HBr*4Br2/SiO2
Solvent CH2Cl2
Time 2 min
Temperature 20 C
Ref. 1 6583579; Journal; Heravi, Majid M.; Derikvand, Fatemeh; Ghassemzadeh, Mitra; SAJCDG; S. Afr. J. Chem.; EN; 59; 2006; 125 - 128.
Reaction Details 2 of 8
Reaction Classification Preparation
Yield 93 percent (BRN=108737)
Reagent hexamethylenetetramine-bromine complex
Solvent CH2Cl2
Temperature 20 C
Ref. 1 6572391; Journal; Heravi, Majid M.; Abdolhosseini, Nafiseh; Oskooie, Hossein A.; TELEAY; Tetrahedron Lett.; EN; 46; 51; 2005; 8959 - 8963.
Reaction Details 3 of 8
Reaction Classification Preparation
Yield 91 percent (BRN=108737)
Reagent 1-butyl-3-methylimidazolium tribromide
Time 5 min
Temperature -10 C
Ref. 1 6488040; Journal; Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo; SYNTBF; Synthesis; EN; 17; 2004; 2809 - 2812.
Reaction Details 4 of 8
Reaction Classification Preparation
Yield 93 percent (BRN=108737)
Reagent NBS
Solvent acetonitrile
Time 17 hour(s)
Temperature 20 C
Ref. 1 6311255; Journal; Canibano, Victoria; Rodriguez, Justo F.; Santos, Mercedes; Sanz-Tejedor, M. Ascension; Carreno, M. Carmen; Gonzalez, Gema; Garcia-Ruano, Jose L.; SYNTBF; Synthesis; EN; 14; 2001; 2175 - 2179.
Reaction Details 5 of 8
Reaction Classification Preparation
Yield 86 percent (BRN=108737)
Reagent bromine
Solvent acetic acid
Time 2 hour(s)
Temperature 20 C
Ref. 1 5632546; Journal; Saidova, F. M.; Binchkauskas, V. Sh.; Khorev, S. G.; Enikeev, E. Ya.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); EN; 17; 2; 1981; 353-357; ZORKAE; Zh. Org. Khim.; RU; 17; 2; 1981; 413-417.
Reaction Details 6 of 8
Reaction Classification Preparation
Yield 53 percent (BRN=108737)
Reagent 3-bromo-6-chloroimidazo<1,2-b>pyridazine hydrobromide-bromine complex
Time 2 hour(s)
Ref. 1 5571197; Journal; Stanovnik, Branko; Tisler, Miha; Drnovsek, Iztok; SYNTBF; Synthesis; EN; 12; 1981; 987-989.
Reaction Details 7 of 8
Reaction Classification Preparation
Reagent diluted aqueous H2SO4
bromine
Ref. 1 1074318; Journal; Bradlow; Vanderwerf; JOCEAH; J. Org. Chem.; 16; 1951; 73, 79.
Reaction Details 8 of 8
Reaction Classification Preparation
Reagent acetic acid
acetic acid anhydride
bromine
Temperature 55 C
Other Conditions Erwaermen des Reaktionsprodukts mit wss.-aethanol. HCl
Ref. 1 987388; Journal; Caldwell et al.; JACSAT; J. Am. Chem. Soc.; 66; 1944; 1479, 1482.
Re: Бромирование по CH-группе аминосодержащих гетероциклов
Бромировать надо 2-аминоиндолизино-1-карбонитрил, достаточно привередливая структура . Формула его висит в Exchange.
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