- Synthesis and antitubercular evaluation of amidoalkyl dibenzofuranols and 1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-ones
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A new class of amidoalkyl dibenzofuranols and 1H-benzo[2,3]benzofuro[4,5-e] [1,3]oxazin-3(2H)-ones was synthesized in very good yields through polyphosphoric acid supported on silica (PPA-SiO2) catalyzed one-pot three component condensation of 2-dibenzofuranol; aromatic aldehydes and acetamide or benzamide or urea under solvent free conditions. At 125 °C the reaction led to the formation of amidoalkyl dibenzofuranols 5a-k where as at 160 °C cyclization take place to give oxazin-3(2H)-one analogues 6a-e. Screening all the 16 compounds for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) resulted 1-((4-chlorophenyl)(2- hydroxydibenzo[b,d]furanyl)methyl)urea 5h; 1-((4-bromophenyl)(2- hydroxydibenzo[b,d]furanyl)methyl)urea 5i; 1-phenyl-1H-benzo[2,3]benzo furo[4,5-e][1,3]oxazin-3(2H)-one 6a (MIC 3.13 μg/mL) and 1-(4-chlorophenyl)- 1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-one 6b; 1-(4-bromophenyl)-1H- benzo[2,3]benzofuro [4,5-e][1,3]oxazin-3(2H)-one 6c (MIC 1.56 μg/mL) as most active antitubercular agents.
- Kantevari, Srinivas,Yempala, Thirumal,Yogeeswari, Perumal,Sriram, Dharmarajan,Sridhar, Balasubramanian
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p. 4316 - 4319
(2011/08/09)
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- A new, one-pot, three-component, solvent-free synthesis of amidoalkyl dibenzofuranols and dibenzofuran-condensed 1,3-oxazin-3-ones
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A new, one-pot, three-component synthesis of amido-alkyl dibenzofuranols and dibenzofuran-condensed 1,3-oxazin-3-ones in good to excellent yields via the reaction of dibenzofuran-2-ol, an aromatic aldehyde, and an amide or urea in the presence of tin(II) chloride dihydrate as a Lewis acid catalyst is described. Georg Thieme Verlag Stuttgart ? New York.
- Kantevari, Srinivas,Yempala, Thirumal,Vuppalapati, Srinivasu V. N.
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experimental part
p. 959 - 966
(2010/05/18)
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