Query 1. Query
Query
Results
Date
IDE.XRN=1736404
7 reactions in Reaxys
2016-06-02 17h:05m:54s (EST)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/5
2016-06-02 17:06:51
O S
Cl
S N
O
N
N
Cl
N S
S O
Rx-ID: 38043377 View in Reaxys 1/7 Yield
Conditions & References
80 %
4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
O S
Cl
S N
O
N
N
Cl
N S
S O
Rx-ID: 38043378 View in Reaxys 2/7 Yield 65 %
Conditions & References 4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/5
2016-06-02 17:06:51
S
Cl
N
O
N
Cl
S
O S N N S O
Rx-ID: 38043380 View in Reaxys 3/7 Yield 74 %
Conditions & References 4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/5
2016-06-02 17:06:51
O
O O
Cl
N
O
N
N
Cl
N
O O
O
Rx-ID: 38043381 View in Reaxys 4/7 Yield
Conditions & References
68 %
4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
O
O O
Cl
O
O
N
O
N
N
Cl
N
O
O
O
O
O
Rx-ID: 38043382 View in Reaxys 5/7 Yield 56 %
Conditions & References 4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/5
2016-06-02 17:06:51
O S
Cl
S N
O
N
N
Cl
N S
S O
Rx-ID: 38043379 View in Reaxys 6/7 Yield
Conditions & References
43 %
4.6. General procedure for the synthesis of 5,11-dialkyl-6,12-di(het)aryl-5,11-dihydroindolo[3,2-b]carbazole-2,8-dicarbaldehydes (5a-f) General procedure: SnCl4 (8 mmol, 2.1 g) was added dropwise to solution of an appropriate indolo[3,2-b]carbazole 3 (1 mmol) and dichloromethyl pentyl ester (8 mmol,1.37 g) in dry 1,2-dichloroethane (20 ml) with stirring at 0 °C and the resulting solution was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice water (100 ml) with concd HCl (2 ml) and vigorously stirred for 2 h. The organic layer was separated and dried with MgSO4. The solvent was removed under vacuum and the solid residue was purified by crystallization from ethyl acetate. The pure dialdehydes were filtrated and washed with methanol (5 ml), and dried at 110 °C for 2 h. With tin(IV) chloride in 1,2-dichloro-ethane, Time= 12h, T= 0 - 20 °C , Rieche Formylation Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron; vol. 70; nb. 31; (2014); p. 4685 - 4696 View in Reaxys
O
O
Cl
O Cl
Rx-ID: 227596 View in Reaxys 7/7 Yield
Conditions & References With phosphorus pentachloride Laato; Suomen Kemistilehti B; vol. 32; (1959); p. 65; ; nb. 49; (1961); p. 35 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/5
2016-06-02 17:06:51