Affiliation:
1. Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab-151302, India
2. Department of Chemistry, Indus International University, V.P.O Bathu, Dist. Una, Himachal Pradesh, Pin-174301, India
3. Department of Physics, University of Jammu, Jammu Tawi-180 006, India
Abstract
Aims:
Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives under greener conditions.
Background:
Quinoxaline and related skeletons are very common in naturally occurring bioactive compounds.
Objective:
Design a facile, green and organo-catalyzed method for the synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives.
Methods:
Both the scaffolds were synthesized via the condensation of ninhydrin and o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of mandelic acid as an efficient, commercially available, low cost, organo-catalyst in aqueous ethanol at room temperature.
Results:
Mild reaction conditions, use of metal-free organocatalyst, non-toxic solvent, ambient temperature, and no column chromatographic separation are some of the notable advantages of our developed protocol.
Conclusion:
In conclusion, we have developed a simple, mild, facile and efficient method for the synthesis of structurally diverse 11H-indeno[1,2-b]quinoxalin-11-one derivatives via the condensation reactions of ninhydrin and various substituted benzene-1,2-diamines using a catalytic amount of mandelic acid as a commercially available metal-free organo-catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives was also accomplished with excellent yields by using pyridine-2,3-diamines instead of o-phenylenediamine.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Analytical Chemistry,Catalysis
Reference65 articles.
1. Watanabe K.; Exploring the biosynthesis of natural products and their inherent suitability for the rational design of desirable compounds through genetic engineering. Biosci Biotechnol Biochem 2008,72(10),2491-2506
2. Pedersen O.S.; Pedersen E.B.; Non-nucleoside reverse transcriptase inhibitors: the NNRTI boom. Antivir Chem Chemother 1999,10(6),285-314
3. Seeler A.O.; Mushett C.W.; Graessle O.; Silber R.H.; Pharmacological Studies on Sulfaquinoxaline. J Pharmacol Exp Ther 1944,82,357-363
4. Kakodkar N.C.; Peddinti R.; Kletzel M.; Tian Y.; Guerrero L.J.; Undevia S.D.; Geary D.; Chlenski A.; Yang Q.; Salwen H.R.; Cohn S.L.; The quinoxaline anti-tumor agent (R+)XK469 inhibits neuroblastoma tumor growth. Pediatr Blood Cancer 2011,56(1),164-167
5. Gao H.; Yamasaki E.F.; Chan K.K.; Shen L.L.; Snapka R.M.; Chloroquinoxaline sulfonamide (NSC 339004) is a topoisomerase IIalpha/β poison. Cancer Res 2000,60(21),5937-5940
Cited by
7 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献