Synthesis of Quinoxalin-2(1H)-ones and Hexahydroquinoxalin-2(1H)-ones via Oxidative Amidation–Heterocycloannulation

Akula Raghunadh; Krishnaji Tadiparthi; Suresh Babu Meruva; V. Narayana Murthy; L. Vaikunta Rao; U. K. Syam Kumar

doi:10.1055/s-0040-1707203

CC BY-NC-ND 4.0 · SynOpen 2020; 04(03): 55-61
DOI: 10.1055/s-0040-1707203

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This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/) (2020) The Author(s)

Synthesis of Quinoxalin-2(1H)-ones and Hexahydroquinoxalin-2(1H)-ones via Oxidative Amidation–Heterocycloannulation

Authors

Akula Raghunadh

^aTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Hyderabad 560049, India
Krishnaji Tadiparthi ∗

^bDepartment of Chemistry, CHRIST (Deemed to be University), Hosur Road, Bangalore 560026, India Email: krishnaji.tadiparthi@christuniversity.in
Suresh Babu Meruva

^aTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Hyderabad 560049, India
V. Narayana Murthy

^aTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Hyderabad 560049, India
L. Vaikunta Rao

^cDepartment of Chemistry, GIS, GITAM University, Visakhapatnam 530045, India
U. K. Syam Kumar∗

^aTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Hyderabad 560049, India

Abstract

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Abstract

A metal-catalyst-free synthesis of substituted quinoxalin-2-ones from 2,2-dibromo-1-arylethanone by employing an oxidative amidation–heterocycloannulation protocol is reported. The substrate scope of the reaction has been demonstrated and a possible mechanism for this reaction has also been proposed.

Key words

oxidative amidation - heterocycloannulation - quinoxalin-2(1H)-one - 2,2-dibromo-1-arylethanone

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References

References

1a Shi L.-L, Zhou H, Wu J.-F, Li X. Mini-Rev. Org. Chem. 2015; 12: 96
1b Carta A, Piras S, Loriga G, Paglietti G. Mini-Rev. Med. Chem. 2006; 6: 1179
1c Li X, Yang K, Li W, Xu W. Drugs Future 2006; 31: 979
1d Akins PT, Atkinson RP. Curr. Med. Res. Opin. 2002; 18: 9
1e Vega AM, Gil MJ, Basilio A, Giraldez A, Fernandez-Alvarez E. Eur. J. Med. Chem. 1986; 21: 251

2a Takeuchi Y, Azuma K, Takakura K, Abe H, Kim H.-S, Wataya Y, Harayama T. Tetrahedron 2001; 57: 1213
2b Taniguchi T, Ogasawara K. Org. Lett. 2000; 2: 3193

3a Sugiura M, Hagio H, Hirabayashi R, Kobayashi S. J. Am. Chem. Soc. 2001; 123: 12510
3b Tekeuchi Y, Abe H, Harayama T. Chem. Pharm. Bull. 1999; 47: 905
3c Kobayashi S, Ueno M, Suzuki R, Ishitani H, Kim H.-S, Wataya Y. J. Org. Chem. 1999; 64: 6833

4a McQuaid LA, Smith EC. R, South KK, Mitch CH, Schoepp DD, True RA, Calligaro DO, Malley PJ. O, Lodge D, Ornstein PL. J. Med. Chem. 1992; 35: 3319
4b Iwata T, Yamagushi M, Hara S, Nakamura M, Ohkura Y. J. Chromatogr. 1986; 362: 209

5a Bourson J, Pouget J, Valeur B. J. Phys. Chem. 1993; 97: 4552
5b Ahmad AR, Mehta LK, Parrick J. Tetrahedron 1995; 51: 12899

6a Smits RA, Lim HD, Hanzer A, Zuiderveld OP, Guaita E, Adami M, Coruzzi G, Leurs R, de Esch IJ. J. Med. Chem. 2008; 51: 2457
6b de la Fuente JR, Canete A, Zanocco AL, Saitz C, Jullian C. J. Org. Chem. 2000; 65: 7949
6c Nunez-Rico JL, Vidal-Ferran A. Org. Lett. 2013; 13: 2066
6d Murthy SN, Madhav B, Nageswar YV. D. Helv. Chim. Acta 2010; 93: 1216
6e Wiedermannová I, Slouka J. J. Heterocycl. Chem. 2001; 38: 1465
6f Zielinski U, Weber FG, Tonew M, Tonew E. Pharmazie 1977; 32: 570
6g Gobec S, Urleb U. Science of Synthesis, Vol. 16. Houben-Weyl Methods of Molecular Transformations, category 2 Georg Thieme; Stuttgart: 2004: 845

7a Brown DJ. Quinoxalines Supplement II . In The Chemistry of Heterocyclic Compounds . Taylor EC, Wipf P. John Wiley & Sons; Hoboken: 2004
7b Heravi MM, Baghernejad B, Oskooie HA. Tetrahedron Lett. 2009; 50: 767
7c Ji Y-F, Chen T.-M, Mao H.-F, Zou J.-P. Chem. Res. Chin. Univ. 2012; 28: 642
7d Yan Y.-M, Li H.-Y, Ren J, Wang S, Ding M.-W. Synlett 2018; 29: 1447
7e Yoshimura M, Ono M, Matsumura K, Watanabe H, Kimura H, Cui M, Nakamoto Y, Togashi K, Okamoto Y, Ihara M, Takahashi R, Saji H. ACS Med. Chem. Lett. 2013; 4: 596

8a Son J.-H, Zhu JS, Phuan P.-W, Cil O, Teuthorn AP, Ku CK, Lee S, Verkman AS, Kurth MJ. J. Med. Chem. 2017; 6: 2401
8b Nagaraj M, Sathiyamoorthy S, Boominathan M, Muthusubramanian S, Bhuvanesh N. J. Heterocycl. Chem. 2013; 50: 1146
8c Gräßle S, Vanderheiden S, Hodapp P, Bulat B, Nieger M, Jung N, Bräse S. Org. Lett. 2016; 18: 3598
8d Dutta NB, Bhuyan M, Baishya G. RSC Adv. 2020; 10: 3615
8e Yan Y.-M, Li H.-Y, Ren J, Wang S, Ding M.-W. Synlett 2018; 29: 1447

9a Murthy VN, Satish NP, Krishnaji T, Madhubabu MV, Rao JS, Rao LV, Raghunadh A. RSC Adv. 2018; 8: 22331
9b Kumar SP, Murthy VN, Ganesh KR, Rao GS, Krishnaji T, Raghunadh A. ChemistrySelect 2018; 3: 6836
9c Jaganmohan C, Kumar KP. V, Reddy GS, Mohanty S, Kumar J, Rao BV, Krishnaji T, Raghunadh A. Synth. Commun. 2018; 48: 168
9d Venkateshwarlu R, Murthy VN, Krishnaji T, Satish PN, Rajesh J, Vidavalur S, Madhu MV, Mohana BH. R, Raghunadh A. RSC Adv. 2020; 10: 9486
9e Jaganmohan Ch, Kumar KP. V, Venkateshwarlu R, Mohanty S, Kumar J, Rao BV, Raghunadh A, Krishnaji T. Synth. Commun. 2020; 14: 2163

10 Raghunadh A, Babu MS, Kumar NA, Kumar GS, Rao LV, Kumar UK. S. Synthesis 2012; 44: 283
11 Makhloufi A, Baitiche M, Merbah M, Benachour D. Synth. Commun. 2011; 41: 3532

Supplementary Material

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