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Water‐Accelerated Cationic π‐(7‐ endo ) Cyclisation: Application to Indole‐Based Peri‐Annulated Polyheterocycles
Author(s) -
Saifuddin Mohammad,
Agarwal Piyush K.,
Sharma Sudhir K.,
Mandadapu Anil K.,
Gupta Sahaj,
Harit Vimal K.,
Kundu Bijoy
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000596
Subject(s) - chemistry , cationic polymerization , indole test , condensation , organic chemistry , catalysis , medicinal chemistry , combinatorial chemistry , thermodynamics , physics
An efficient and versatile method for the synthesis of indole‐based polycyclic indolo‐benzazepine and its derivatives through water‐accelerated cationic π‐cyclisation is described. The strategy involves condensation of arylamine moieties linked to C‐4 in indole/azaindole systems with arylaldehydes in water containing catalytic amount of Brønsted acids. The C–C bond formation in water is complete within 10–30 min, furnishing the title compounds in excellent yields and purities, whereas in organic solvents 10–12 h are required. Furthermore, aldehydes both with electron‐donating and‐withdrawing substituents facilitate the π‐cyclisation equally.