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Synthesis of novel and biologically potent heteropolycyclics containing bridge head nitrogen
Author(s) -
Gupta Poonam,
Gupta Shallu,
Sachar Anand,
Sharma R. L.
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.465
Subject(s) - chemistry , diazepine , ethylene glycol , condensation , tricyclic , nitrogen , catalysis , imidazole , pyrimidine , ring (chemistry) , solvent , organic chemistry , combinatorial chemistry , stereochemistry , physics , thermodynamics
AbstractA facile one pot synthesis of 2,3,4,5‐tetrahydropyrido [1,2‐ a ] [1,3] diazepine‐2,5‐dione 2 and 3,4‐dihydro‐2 H ‐pyrido [1,2‐ a ] pyrimidine‐2,4‐dione 3 has been achieved. Condensation of 3 with o ‐aminobenzaldehydes produced the linear product 4 and not the angular one 5 . Cyclocondensation of 3 with 1,5‐diketones afforded a tricyclic linear system 6 , a bis assembly system 7 and two novel heterotetracyclic nitrogen bridged linear systems 8 and 10 . Condensation of o ‐aminobenzaldehydes with 2 produced a novel linear system 12 and a new doubly fused hexacyclic system 11 . Cyclodehydration of 2 with 1,2‐dicarbaldehydes produced 1 , 13 , and a new heterotetracyclic nitrogen bridged system 14 . Condensation of 3 with aromatic aldehydes in presence of ethylene glycol as solvent without the use of catalyst generated the doubly nitrogen bridged linear pentacyclic systems 15 , 16 , 17 . The synthesized compounds have been adequately characterized and screened for bronchodilatory and antimicrobial activities with promising results. J. Heterocyclic Chem., (2010).