z-logo
Premium
Chemical behavior of 4, 9‐dimethoxy‐5‐oxo‐5 H ‐furo[3,2‐ g ]chromene‐6‐carboxaldehyde towards carbon nucleophilic reagents
Author(s) -
Ibrahim Magdy A.,
ElGohary Nasser M.
Publication year - 2020
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.3991
Subject(s) - chemistry , malononitrile , pyridine , nucleophile , methylene , reagent , ring (chemistry) , aldehyde , cyanoacetamide , medicinal chemistry , benzimidazole , organic chemistry , stereochemistry , catalysis
The chemical behavior of 6‐formylkhellin ( 1 ) was investigated toward a variety of carbon nucleophiles. Treatment of aldehyde 1 with cyanoacetamide, N ‐benzylcyanoacetamide produced pyridine‐3‐carboxamides 3 and 4 . Treatment of carboxaldehyde 1 with malononitrile dimer and 1 H ‐benzimidazol‐2‐ylacetonitrile gave 1,6‐naphthyridine 5 and pyrido[1,2‐ a ]benzimidazole 6 , respectively. Some novel pyrazolo[3,4‐ b ]pyridine 7 , pyrido[2,3‐ d ]pyrimidines 8 and 9 were synthesized from the ring opening ring closure reactions of carboxaldehyde 1 with certain heterocyclic enamines. In addition, reaction of carboxaldehyde 1 with certain cyclic enols produced a variety of products. Treatment of carboxaldehyde 1 with 1,3‐cyclohexanediones gave xanthene‐1,8‐diones 19 and 20 . Reaction of carboxaldehyde 1 with 5‐methyl‐2,4‐dihydro‐3 H ‐pyrazol‐3‐one proceeds in 1:2 M ratio producing pyrazolo [4′,3′:5,6]pyrano[2,3‐ c ]pyrazole derivative 22 . Carboxaldehyde 1 reacted with certain heterocyclic compounds containing active methylene groups to give the corresponding condensation products 22 ‐ 27 . The synthesized compounds were screened in vitro for their antimicrobial activity and showed high to moderate activities against the tested microorganisms.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here