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Regioselective Synthesis of Quinazolinone‐/Phenanthridine‐Fused Heteropolycycles by Pd‐Catalyzed Direct Intramolecular Aerobic Oxidative C−H Amination from Aromatic Strained Amides
Author(s) -
Banerji Biswadip,
Bera Suvankar,
Chatterjee Satadru,
Killi Sunil Kumar,
Adhikary Saswati
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504186
Subject(s) - phenanthridine , quinazolinone , regioselectivity , amination , chemistry , intramolecular force , amide , aromaticity , combinatorial chemistry , palladium , amidine , molecule , organic chemistry , catalysis
A new route for the expedient synthesis of specific regioisomer of quinazolinone‐ and phenanthridine‐fused heterocycles through a palladium‐catalyzed regioselective intramolecular oxidative C−H amination from cyclic strained amides of aromatic amido–amidine systems (quinazolinones) has been developed. The amine functionalization of an aromatic C−H bond from a strained amide nitrogen involved in aromaticity has been a challenging work so far. The fusion of two heterocyclic cores, quinazolinone and phenanthridine, can occur in two different ways (linear and angular), but under the conditions reported here, only linear type isomer is exclusively produced. This approach provides a variety of substituted quinazolinone‐ and phenanthridine‐fused derivatives in moderate to excellent yields. Moreover, such fused molecules show excellent fluorescent properties and have great potential to be a new type of fluorophores for the use in medicinal and material science.