Microwave Promoted One-Pot Synthesis of Some NovelN-Aryl Isoquinoline Derivatives

Abstract

Homophthalic anhydride 1 reacts with different aromatic amines to produce N‐substituted homophthalimides 2 under microwave irradiation. A rapid microwave‐assisted chemical synthesis of condensed 4‐substituted furo[2,3‐c]isoquinoline‐1,5(2H,4H)‐diones 3 and 5‐substituted‐2,3‐dihydro‐1H‐pyrano[2,3‐c]isoquinoline‐1,6(5H)‐diones 4 involving the condensation of a variety of alkanoyl chlorides with 2‐arylisoquinoline‐1,3‐diones 2 in the presence of base and aprotic solvent is described for the first time. By contrast, the facile ring opening reaction of furo[2,3‐c]isoquinoline‐1,5(2H,4H)‐dione 3 with Vilsmeier–Haack reagent under microwave irradiation yielded the α‐β unsaturated carboxyaldehyde 5. This novel and clean one‐pot methodology, which is characterized by very short reaction time and easy workup procedure, can be exploited to generate some novel condensed isoquinoline derivatives.

Synthesis and antibacterial activity of some heterocyclic derivatives of sulfanilamide

“…The synthesized compounds exhibited characteristic IR (KBr, ν cm For the in vitro screening pure strains were obtained from Post Graduate Department of Microbiology, Orissa University of Agricultural Technology, Bhubaneswar, India. The organisms were identified [7] and screened using disc diffusion method [11][12]. The compounds were dissolved in dimethyl formamide (6%), which was previously tested for antibacterial activity against all test bacteria and found to have no antibacterial activity.…”

“…Synthesis of compound 1 and 2a-e were done as per the reported method [7][8] with little modification. (1).…”

“…Conjugations of heterocyclic groups reportedly enhance antibacterial action of the original compound [6]. Besides derivatives of azetidinone, thiazolidinone [7], oxazoles [8] and imidazoles [9] are widely reported with antibacterial action. It is thus envisageable that conjugation of heterocyclic compounds with sulfanilamide will be able to enhance the antibacterial action of sulfanilamide leading to novel types of pharmacological agents useful in the fight against infections.…”

3-Chloropropionyl Chloride

“…2 (B) A novel high-yielding one-pot microwave-assisted synthesis of condensed 5-substituted pyranoisoquinoline-1,6-diones 9 from 2-substituted isoquinoline-1,3-diones 8 and 3-chloropropionyl chloride (1) was reported. 3 (C) Aouf et al reported the titanium tetrachloride mediated addition of 3-chloropropionyl chloride (1) to 2,3,6,7-tetramethyl-1,8-bis(trimethylsilyl)-octa-2,6-diene (10) leading to cyclopentanol derivative 11, which contains three quaternary carbons. 4 Cl Cl …”