Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00032269.xml
Download PDF
CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0138-0144
DOI: 10.1055/s-0036-1591572
DOI: 10.1055/s-0036-1591572
paper
Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating Agent
Authors
C.C.M. acknowledges Science and Engineering Research Board (SERB), New Delhi and NIT Manipur for the financial support in the form of research grant (ECR/2016/000337). R.G., N.V., D.K. and A.K.K. are grateful to the Ministry of Human Resource and Development (MHRD), New Delhi for Fellowship support.
Further Information
Publication History
Received: 31 January 2018
Accepted after revision: 05 April 2018
Publication Date:
09 May 2018 (online)
Abstract
Molybdenum(VI)-catalyzed domino reductive cyclization of nitroarenes has been devised for the syntheses of 1,4-benzoxazines and 1,4-benzothiazines in the presence of pinacol as deoxygenating agent. The scope of the described method was further extended to the syntheses of the rarely explored scaffolds, 1-hydroxyphenazines and quinoxalines. The present method avoids the use of hazardous deoxygenating agents and operates under solvent-free conditions.
Key words
N-heterocycles - domino reaction - reductive cyclization - nitroarenes - dioxo-Mo(VI) complex - pinacolSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591572.
- Supporting Information (PDF)
-
References
- 1a Royer J. Asymmetric Synthesis of Nitrogen Heterocycles . Wiley-VCH Verlag; Weinheim: 2009
- 1b Huang Y. Khoury K. Dömling A. In Synthesis of Heterocycles via Multicomponent Reactions I . Vol. 23. Orru RV. A. Ruijter E. Springer; Berlin, Heidelberg: 2010: p 85
- 1c Wolfe JP. Neukom JD. Mai DH. Synthesis of Saturated Five-Membered Nitrogen Heterocycles via Pd-Catalyzed C–N Bond-Forming Reactions. Wiley-VCH Verlag; Weinheim: 2011
- 1d Eicher T. Hauptmann S. Speicher A. Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications . Wiley; Somerset, NJ: 2013
- 1e Wolfe JP. Synthesis of Heterocycles via Metal-Catalyzed Reactions That Generate One or More Carbon–Heteroatom Bonds. Springer; Berlin, Heidelberg: 2013
- 1f Sammes PG. Chem. Rev. 1976; 76: 113
- 1g Fodor L. Szabó J. Bernáth G. Sohár P. Maclean DB. Smith RW. Ninomiya I. Naito T. J. Heterocycl. Chem. 1989; 26: 333
- 1h Diurno MV. Mazzoni O. Izzo AA. Bolognese A. Farmaco 1997; 52: 257
- 1i Cecchetti V. Filipponi E. Fravolini A. Tabarrini O. Xin T. Bioorg. Med. Chem. 1997; 5: 1339
- 1j Deziel R. Malenfant E. Bioorg. Med. Chem. Lett. 1998; 8: 1437
- 1k Armenise D. Trapani G. Stasi F. Morlacchi F. Arch. Pharm. 1998; 331: 54
- 1l Feher M. Schmidt JM. J. Chem. Inf. Comput. Sci. 2002; 43: 218
- 1m Hilton ST. Motherwell WB. Potier P. Pradet C. Selwood DL. Bioorg. Med. Chem. Lett. 2005; 15: 2239
- 1n Song Z.-C. Ma G.-Y. Lv PC. Li HQ. Xiao ZP. Zhu HL. Eur. J. Med. Chem. 2009; 44: 3903
- 1o Gomez- MonterreyI. Bertamino A. Porta A. Carotenuto A. Musella S. Aquino C. Granata I. Sala M. Brancaccio D. Picone D. Ercole C. Stiuso P. Campiglia P. Grieco P. Ianelli P. Maresca B. Novellino E. J. Med. Chem. 2010; 53: 8319
- 1p Kaur SP. Rao R. Nanda S. Int. J. Pharm. 2010; 402: 37
- 1q Leeson PD. St-Gallay SA. Wenlock MC. MedChemComm 2011; 2: 91
- 1r Kaur SP. Rao R. Nanda S. Int. J. Pharm. Pharm. Sci. 2011; 3: 30
- 1s Jarvis CL. Richers MT. Breugst M. Houk KN. Seidel D. Org. Lett. 2014; 16: 3556
- 1t Feng H. Jia H. Sun Z. Adv. Synth. Catal. 2015; 357: 2447
- 2a Lovering F. Bikker J. Humblet C. J. Med. Chem. 2009; 52: 6752
- 2b Schnurch M. Dastbaravardeh N. Ghobrial M. Mrozek BD. Mihovilovic M. Curr. Org. Chem. 2011; 15: 2694
- 2c Ritchie TJ. Macdonald SJ. F. Young RJ. Pickett SD. Drug Discovery Today 2011; 16: 164
- 2d Zhu Z. Tang X. Li J. Li X. Wu W. Deng G. Jiang H. Org. Lett. 2017; 19: 1370
- 2e Song P. Yu P. Lin J.-S. Li Y. Yang N.-Y. Liu X.-Y. Org. Lett. 2017; 19: 1330
- 2f Yan F. Liang H. Song J. Cui J. Liu Q. Liu S. Wang P. Dong Y. Liu H. Org. Lett. 2017; 19: 86
- 3a Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010; 110: 624
- 3b Engle KM. Mei TS. Wasa M. Yu J.-Q. Acc. Chem. Res. 2011; 45: 788
- 3c Lu P. Wang Y. Chem. Soc. Rev. 2012; 41: 5687
- 3d El-salam NM. A. Mostafa MS. Ahmed GA. Alothman OY. J. Chem. 2013; 1
- 3e Azab ME. Youssef MM. El-Bordany EA. Molecules 2013; 18: 832
- 3f Salem MS. Sakr SI. El-Senousy WM. Madkour HM. F. Arch. Pharm. (Weinheim) 2013; 346: 766
- 3g Xu X. Doyle MP. Acc. Chem. Res. 2014; 47: 1396
- 3h Xie J. Pan C. Abdukadera A. Zhu C. Chem. Soc. Rev. 2014; 43: 5245
- 3i Cao X. Sun Z. Cao Y. Wang R. Cai T. Chu W. Hu W. Yang Y. J. Med. Chem. 2014; 57: 3687
- 3j Chen Y. Yu K. Tan NY. Qiu RH. Liu W. Luo NL. Tong L. Au CT. Luo ZQ. Yin SF. Eur. J. Med. Chem. 2014; 79: 391
- 3k Sharma UK. Sharma N. Vachhani DD. der Eycken EV. V. Chem. Soc. Rev. 2015; 44: 1836
- 3l Yang L. Huang H. Chem. Rev. 2015; 115: 3468
- 3m Martins P. Jesus J. Santos S. Raposo LR. Roma-Rodrigues C. Baptista PV. Fernandes AR. Molecules 2015; 20: 16852
- 3n Yu J.-T. Pan C. Chem. Commun. 2016; 2220
- 4a Felpin F.-X. Lebreton J. Eur. J. Org. Chem. 2003; 3693
- 4b Ragaini F. Cenini S. Brignoli D. Gasperini M. Gallo E. J. Org. Chem. 2003; 68: 460
- 4c Smitrovich JH. Davies IW. Org. Lett. 2004; 6: 533
- 4d Pyne SG. Davis AS. Gates NJ. Hartley JP. Lindsay KB. Machan T. Tang M. Synlett 2004; 2670
- 4e Coldham I. Hufton R. Chem. Rev. 2005; 105: 2765
- 4f Bellina F. Rossi R. Tetrahedron 2006; 62: 7213
- 4g Merisor E. Conrad J. Klaiber I. Mika S. Beifuss U. Angew. Chem. Int. Ed. 2007; 46: 3353
- 4h Merisor E. Conrad J. Mika S. Beifuss U. Synlett 2007; 2033
- 4i Merisor E. Beifuss U. Tetrahedron Lett. 2007; 48: 8383
- 4j Ferretti F. Formenti D. Ragaini F. Rend. Lincei 2017; 28: 97
- 4k El-Atawy MA. Ferretti F. Ragaini F. Eur. J. Org. Chem. 2017; 1902
- 4l Formenti d. Ferretti F. Ragaini F. ChemCatChem 2018; 10: 148
- 5 Mali M. Synth. Catal. 2017; 2: 2
- 6a Cadogan JI. G. Cameron-Wood M. Proc. Chem. Soc. (London) 1962; 361
- 6b Cadogan JI. G. Cameron-Wood M. Mackie RK. Searle RJ. G. J. Chem. Soc. 1965; 4831
- 6c Sundberg RJ. Tetrahedron Lett. 1965; 477
- 6d Cadogan JI. G. Todd MJ. J. Chem. Soc. C 1969; 2808
- 6e Ho TL. Hsieh SY. Helv. Chim. Acta 2006; 89: 111
- 6f Freeman AW. Urvoy M. Criswell ME. J. Org. Chem. 2005; 70: 5014
- 6g Sanz R. Escribano J. Pedrosa MR. Aguado R. Arnaiz FJ. Adv. Synth. Catal. 2007; 349: 713
- 7a Crotti C. Cenini S. Rindone B. Tollari S. Demartin F. J. Chem. Soc., Chem. Commun. 1986; 784
- 7b Annunziata R. Cenini S. Palmisano G. Tollari S. Synth. Commun. 1996; 26: 495
- 7c Söderberg BC. G. Wallace JM. Tamariz J. Org. Lett. 2002; 4: 1339
- 7d Scott TL. Söderberg BC. G. Tetrahedron Lett. 2002; 43: 1621
- 7e Han R. Chen S. Lee SJ. Qi F. Wu X. Kim BH. Heterocycles 2006; 68: 1675
- 7f Wallace JM. Söderberg BC. G. Tamariz J. Akhmedov NG. Hurley MT. Tetrahedron 2008; 64: 9675
- 8a Fernandes AC. Romáo CC. Tetrahedron 2006; 62: 9650
- 8b Fernandes AC. Romáo CC. Tetrahedron Lett. 2007; 48: 9176
- 8c Reis PM. Costa PJ. Romáo CC. Fernandes JA. Calhorda MJ. Royo B. Dalton Trans. 2008; 1727
- 8d Reis PM. Royo B. Tetrahedron Lett. 2009; 50: 949
- 9a Alper H. Edward JT. Can. J. Chem. 1970; 48: 1543
- 9b Crotti C. Cenini S. Bossoli A. Rindone B. Demartin F. J. Mol. Catal. 1991; 70: 175
- 9c Pizzotti M. Cenini S. Quici S. Tollari S. J. Chem. Soc., Perkin Trans. 2 1994; 913
- 9d For a review, see: Söderberg BC. G. Curr. Org. Chem. 2000; 4: 727
- 9e Smitrovich JH. Davies IW. Org. Lett. 2004; 6: 533
- 9f Vodnala N. Kaldhi D. Polina S. Putta VP. R. K. Gupta R. Promily SC. P. Linthoinganbi RK. Singh V. Malakar CC. Tetrahedron Lett. 2016; 57: 5695
- 10a Pizzotti M. Cenini S. Psaro R. Costanzi S. J. Mol. Catal. 1990; 63: 299
- 10b Crotti C. Cenini C. J. Chem. Soc., Faraday Trans. 1991; 87: 2811
- 10c Crotti C. Cenini S. Ragaini F. Porta F. Tollari S. J. Mol. Catal. 1992; 72: 283
- 11 Sanz R. Escribano J. Aguado R. Pedrosa MR. Arnáiz FJ. Synthesis 2004; 1629
- 12a Malakar CC. Merisor E. Conrad J. Beifuss U. Synlett 2010; 1766
- 12b Moustafa AH. Malakar CC. Aljaar N. Merisor E. Conrad J. Beifuss U. Synlett 2013; 24: 1573
- 12c Siddiqui IR. Srivastava A. Singh A. Shamim S. Rai P. RSC Adv. 2015; 5: 5256
- 12d Vodnala N. Kaldhi D. Gupta R. Polina S. Putta VP. R. K. Promily SC. P. Linthoinganbi RK. Singh V. Malakar CC. ChemistrySelect 2016; 1: 5784
- 13 Garcia N. Garcia-Garcia P. Fernindez-Rodriguez MA. Rubio R. Pedrosa MR. Arnaiz FJ. Sanz R. Adv. Synth. Catal. 2012; 354: 321; and references cited therein
- 14 Gerber NN. J. Org. Chem. 1967; 32: 4055
- 15 Toshima K. Takano R. Ozawa T. Matsumura S. Chem. Commun. 2002; 212
- 16a Anderson RK. Carter SD. Cheeseman GW. H. Tetrahedron 1979; 35: 2463
- 16b Zhang Z. Yin Z. Kadow JF. Meanwell NA. Wang T. Synlett 2004; 2323