Abstract
A unique one-pot, simultaneous nitrodebromination and methyl bromonitration occurred upon treatment of 5-bromo-2,4-di-tert-amino-6-methylpyrimidine derivatives with a cold mixture of concentrated H2SO4–HNO3 in moderate yields. It is actually a facile and rapid transformation that has been reported neither on pyrimidines nor simultaneously on other organic compounds.
Graphic abstract
Similar content being viewed by others
References
Heravi MM, Zadsirjan V, Malmir M (2018) Molecules 23:943
Heravi MM, Zadsirjan V, Hamidi H, Hajiabbas TAP (2017) RSC Adv 7:24470
Heravi MM, Lashaki BT, Poorahmad N (2015) Tetrahedron: Asymmetry 26:405
Ono N (2001) The nitro group in organic synthesis. Wiley-VCH, New York
Soengas RG, Acurcio RC, Silva AM (2014) Eur J Org Chem 2014:6339
Hernandes MZ, Cavalcanti SMT, Moreira DRM, de Azevedo J, Filgueira W, Leite ACL (2010) Curr Drug Targets 11:303
Sen S, Kamm SR, Potti VR, Murthy YLN, Chaudhary AB (2011) Tetrahedron Lett 52:5585
Butler P, Golding BT, Laval G, Loghmani-Khouzani H, Ranjbar-Karimi R, Sadeghi MM (2007) Tetrahedron 63:11160
Feuer H, Lawrence JP (1972) J Org Chem 37:3662
Wu D, Zhang J, Cui J, Zhang W, Liu Y (2014) Chem Commun 50:10857
Kurfürst A, Schwarz M (1989) Collect Czech Chem Commun 54:1346
Kurfürst A, Raclová F, Kuthan J (1980) Collect Czech Chem Commun 45:397
Stock NS, Bain G, Zunic J, Li Y, Ziff J, Roppe J, Santini A, Darlington J, Prodanovich P, King CD, Baccei C (2011) J Med Chem 54:8013
Su N, Bradshaw JS, Zhang XX, Song H, Savage PB, Xue G, Krakowiak KE, Izatt RM (1999) J Org Chem 64:8855
Adhikari S, Mandal S, Ghosh A, Das P, Das D (2015) J Org Chem 80:8530
Maj AM, Suisse I, Hardouin C, Agbossou-Niedercorn F (2013) Tetrahedron 69:9322
Wang L, Hou X, Fu H, Pan X, Xu W, Tang W, Fang H (2015) Bioorg Med Chem 23:4364
Shults MD, Imperiali B (2003) J Am Chem Soc 125:14248
Bi WZ, Qu C, Chen XL, Wei SK, Qu LB, Liu SY, Sun K, Zhao YF (2018) Tetrahedron 74:1908
Xie Y, Li L (2014) Tetrahedron Lett 55:3892
Priyadarshini S, Joseph PA, Kantam ML, Sreedhar B (2013) Tetrahedron 69:6409
Ravi P, Tewari SP (2013) Catal Commun 42:35
Paik SU, Jung MG (2012) Bull Korean Chem Soc 33:689
Ravi P, Gore GM, Sikder AK, Tewari SP (2012) Synth Commun 42:3463
Wu X, Dube MA, Fry AJ (2006) Tetrahedron Lett 47:7667
Chang K, Grimmett MR, Ward DD, Weavers RT (1979) Aust J Chem 32:1727
Clewley RG, Fischer A, Henderson GN (1989) Can J Chem 67:1472
Reznikov VA, Vishnivetskaya LA, Volodarsky LB (1994) Russ Chem Bull 43:275
Russell G, Dedolph D (1985) J Org Chem 50:2498
Feuer H, Friedman H (1975) J Org Chem 40:187
Feuer H, Vincent EF (1964) J Org Chem 29:939
Terentev AO, Krylov IB, Ogibin YN (2006) Synthesis 2006:3819
Marchand AP, Arney BE Jr, Dave PR (1988) J Org Chem 53:443
Mousavi M, Bakavoli M, Shiri A, Eshghi H (2018) ACS Sustainable Chem Eng 6:5852
Heravi MM, Benmorad T, Bakhtiari Kh, Bamoharram FF, Oskooie H (2007) J Mol Catal A-Chem 264:318
Heravi MM, Abdolhosseini N, Oskooie H (2005) Tetrahedron Lett 46:8959
Bakavoli M, Rahimizadeh M, Shiri A, Eshghi H, Vaziri-Mehr S, Pordeli P, Nikpour M (2011) Heterocycl Commun 17:49
Eshghi H, Rahimizadeh M, Saberi S, Abnous K, Bakavoli M (2013) J Chem Res 37:553
Bazazan T, Bakavoli M, Rahimizadeh M, Eshghi H, Nikpour M (2013) Heterocycl Commun 19:401
Ebrahimpour Z, Shiri A, Bakavoli M, Seyedi SM, Asghari T, Mague J (2017) J Heterocycl Chem 54:235
Igei M, Bakavoli M, Shiri A, Ebrahimpour Z, Azizollahi H, Beyzaei H, Moghaddam-Manesh M (2016) J Chem Res 40:628
Mousavi M, Bakavoli M, Shiri A, Tajabadi J (2018) Chemistry Select 3:5401
Tajabadi J, Bakavoli M, Gholizadeh M, Eshghi H, Izadyar M (2015) RSC Adv 5:38489
Bakavoli M, Eshghi H, Shiri A, Afrough T, Tajabadi J (2013) Tetrahedron 69:8470
Lodewyk MW, Siebert MR, Tantillo DJ (2012) Chem Rev 112:1839
Minkin VI, Mikhailov IE, Dushenko GA, Yudilevich JA, Minyaev RM, Zschunke A, Mögge K (1991) J Phys Org Chem 4:31
Ditchfield R (1974) Mol Phys 27:789
Sarotti AM, Pellegrinet SCA (2009) J Org Chem 74:7254
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb, MA, Cheeseman JR, Scalmani G, Barone V, Mennucci, B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A.02. Gaussian, Inc, Wallingford, CT
Acknowledgements
M. M. acknowledges the Research Council of Ferdowsi University of Mashhad for partial support of this project (3/33579). M. M. H. is grateful to Alzahra University Research Council as well as appreciates the granted research chair by Iran National Science Foundation (INSF).
Author information
Authors and Affiliations
Corresponding authors
Additional information
In memory of professor Mehdi Bakavoli, who was skilled, mastered, and proficient at pyrimidine chemistry.
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Mousavi, M., Heravi, M.M. & Tajabadi, J. One-pot nitrodebromination and methyl bi-functionalization of 5-bromo 6-methylpyrimidines: a unique simultaneous transformation. Monatsh Chem 151, 1395–1401 (2020). https://doi.org/10.1007/s00706-020-02658-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-020-02658-7