Free radical intramolecular cyclization in the synthesis of heterocycles (review)

1993 ◽  
Vol 29 (8) ◽  
pp. 857-877
Author(s):  
S. S. Zlot-skii ◽  
M. V. Kochinashvili ◽  
D. L. Rakhmankulov
Keyword(s):  
Free Radical ◽  
Intramolecular Cyclization

Free radical synthesis of benzofused tricyclic β-lactams by intramolecular cyclization of 2-azetidinone-tethered haloarenes

Tetrahedron ◽  
2005 ◽  
Vol 61 (11) ◽  
pp. 2767-2778 ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
Alberto Rodríguez-Vicente ◽  
M. Pilar Ruiz
Keyword(s):  
Free Radical ◽  
Intramolecular Cyclization

ChemInform Abstract: Free Radical Intramolecular Cyclization in the Synthesis of Heterocycles

ChemInform ◽  
2010 ◽  
Vol 25 (20) ◽  
pp. no-no
Author(s):  
S. S. ZLOTSKII ◽  
M. V. KOCHINASHVILI ◽  
D. L. RAKHMANKULOV
Keyword(s):  
Free Radical ◽  
Intramolecular Cyclization

Free Radical Synthesis of Benzofused Tricyclic β-Lactams by Intramolecular Cyclization of 2-Azetidinone-Tethered Haloarenes.

ChemInform ◽  
2005 ◽  
Vol 36 (30) ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
Alberto Rodriguez-Vicente ◽  
M. Pilar Ruiz
Keyword(s):  
Free Radical ◽  
Intramolecular Cyclization

scholarly journals Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

2021 ◽  
Vol 17 ◽  
pp. 1490-1498
Author(s):  
Ivan P Mosiagin ◽  
Olesya A Tomashenko ◽  
Dar’ya V Spiridonova ◽  
Mikhail S Novikov ◽  
Sergey P Tunik ◽  
...  
Keyword(s):  
Free Radical ◽  
Intramolecular Cyclization ◽  
Room Temperature ◽  
Radical Cyclization ◽  
Quantitative Yield ◽  
Pyridinium Bromide ◽  
Wide Range ◽  
Selectivity Control ◽  
Isoquinoline Derivatives ◽  
Dibromo Derivative

A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides having no additional radical-sensitive substituents. The free bases can be obtained from the synthesized hydrobromides in quantitative yield by basification at room temperature. The selectivity control of intramolecular arylation was achieved by replacing the halogen: the use of 1-(2-(ortho-bromophenyl)-4-(ortho-iodophenyl)pyrrol-3-yl)pyridinium bromide makes it possible to obtain a monocyclization product, and the bicyclization product from the dibromo derivative. The procedure is also applicable to obtain 3-arylpyrido[2,1-a]pyrrolo[3,2-c]isoquinoline derivatives including 2-unsubstituted skeletons that are inaccessible via Pd-catalyzed cyclization.

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