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Synthesis 2017; 49(16): 3768-3774
DOI: 10.1055/s-0036-1588825
DOI: 10.1055/s-0036-1588825
paper
An Efficient and Concise Synthesis of N-3-Substituted 9-Methoxy-4H-[1]-benzopyrano[2,3-d]pyrimidine-4(5H)-imines and Formamidine Derivatives from Methyl N-(3-Cyano-8-methoxy-4H-[1]-benzopyran-2-yl)methanimidate
Further Information
Publication History
Received: 06 March 2017
Accepted after revision: 10 April 2017
Publication Date:
18 May 2017 (online)
Abstract
A four-step microwave-assisted reaction of N-3-susbstituted 4H-[1]-benzopyrano[2,3-d]pyrimidine-4(5H)-imines and formamidine derivatives was successfully developed from primary amines, cyclic secondary amines, and methyl N-(3-cyano-8-methoxy-4H-[1]-benzopyran-2-yl)methanimidate as key intermediate. The simplicity of the microwave protocols gave facile possibilities of isolation of the desired products by simple filtration. The synthesized compounds were obtained in good yields and purity, and characterized by 1H, 13C NMR, IR, and HRMS analyses.
Key words
microwave irradiation - benzopyranopyrimidine-4-imine - (benzopyran-2-yl)methanimidate - formamidine - solvent-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588825.
- Supporting Information
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References
- 1a Thirupathaiah B. Reddy MV. Jeong YT. Tetrahedron 2015; 71: 2168
- 1b Brahmachari G. Trends Green Chem. 2015; 1: 1
- 1c Brahmachari G. Das S. J. Heterocycl. Chem. 2015; 52: 653
- 1d Shaikh TS. Patil DS. Gaikwad DS. Hegade PG. Patil PB. Undale KA. Mane MM. Pore DM. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2014; 53: 1288
- 1e Zozouni A. Hosseinzadeh F. Karimi N. Mirzazadeh R. Ng SW. ACS Comb. Sci. 2013; 15: 240
- 1f Tavakoli HR. Moosavi SM. Bazgir A. J. Korean Chem. Soc. 2013; 57: 260
- 1g Gupta AK. Kumari K. Singh N. Raghuvanshi DS. Singh KN. Tetrahedron Lett. 2012; 53: 650
- 1h Ghahremanzadeh R. Amanpour T. Bazgir A. Tetrahedron Lett. 2010; 51: 4202
- 2a Hatem AA. M. Asian J. Pharm. Clin. Res. 2015; 8: 7
- 2b Bruno O. Brullo C. Schenone S. Bondavalli F. Ranise A. Tognolini M. Impicciatore M. Ballabeni V. Baroicelli E. Bioorg. Med. Chem. 2006; 14: 121
- 2c Balladeni V. Calcina F. Tognolini M. Bruno O. Manotti C. Barocelli E. Life Sci. 2004; 74: 1851
- 3 Dgachi Y. Ismaili L. Knez D. Benchekroun M. Martin H. Szalaj N. Wehle S. Bautista-Aguilera OM. Luzet V. Bonnet A. Malawska B. Gobec S. Chioua M. Decker M. Chabchoub F. Marco-Contelles J. ChemMedChem 2016; 11: 1318
- 4 Mc Coy JG. Marugan JJ. Liu K. Zheng W. Southall N. Huang W. Heilig M. Austin CP. ACS Chem. Neurosci. 2010; 1: 559
- 5 Bazureau J.-P. Paquin L. L’Helgoual’ch J.-M. Carrie D. Limanton E. Guiheneuf S. Burgy G. Coulibaly W.-K. Komaty S. In Microwaves in Organic Chemistry . 3rd ed.; Loupy A. de La Hoz A. Wiley-VCH; Weinheim: 2012: 673
- 6 Vanden Eynde JJ. Pharmaceuticals 2016; 9: 26
- 7a Fakhfakh M. Turki H. Fery-Forgues S. El-Gharbi R. Dyes Pigm. 2010; 84: 108
- 7b Turki H. Abid S. Le Bigot Y. Fery-Forgues S. El-Gharbi R. Synth. Commun. 2004; 34: 3553
- 8 Dunn PJ. In Comprehensive Organic Functional Group Transformations II . Vol. 5. Katritzky AR. Taylor RJ. Elsevier; Amsterdam: 2005: 655
- 9a Mohammed FK. Badrey MG. J. Korean Chem. Soc. 2011; 55: 218
- 9b El-Agrody AM. Emam HA. El-Hakim MH. Abd El-Latif MS. Fakery AH. J. Chem. Res. 1997; 320
- 10 Salem M. Chabchoub F. Messaâd M. Heterocycl. Commun. 2005; 11: 139
- 11 El-Khawaga AM. El-Zohry M. Mohamed TA. Hussein E. Heterocycl. Commun. 2010; 16: 157
- 12 Hollo B. Leovac VM. Bombicz P. Kovacs A. Jovanovic LS. Bogdanovic G. Kojic V. Divjakovic V. Joksovic MD. Szecsenyi KM. Aust. J. Chem. 2010; 63: 1557
- 13 Balog J. Riedl Z. Hajos G. Tetrahedron Lett. 2013; 54: 5338
- 14a Besson T. Fruit C. Synthesis 2016; 48: 3879
- 14b Larhed M. Hallberg A. Drug Discovery Today 2001; 6: 406
- 15 Dallinger D. Lehmann H. Moseley JD. Stadler A. Kappe CO. Org. Process Res. Dev. 2011; 15: 841
- 16 Kandeel MM. Kamal AM. Abdelall EK. A. Elshemy HA. H. Pharm. Chem. 2012; 4: 1653
- 17 Jouno S. Bazureau J-P. Tetrahedron Lett. 1999; 40: 8097
- 18a Naert G. Ferré V. Meunier J. Keller E. Malmström S. Givalois L. Carreaux F. Bazureau J.-P. Maurice M. Eur. Neuropsychopharm. 2015; 25: 2170
- 18b Tahtouh T. Federov O. Soundararajan M. Burgy G. Durieu E. Lozach O. Cochet C. Schmid RS. Lo DC. Delhommel F. Oberholzer AE. Pearl LH. Carreaux F. Bazureau J.-P. Knapp S. Meijer L. J. Med. Chem. 2012; 55: 9312
- 19 Ambeu NtaC. Dago C-D. Coulibaly W-K. Mamyrbekova-Bekro JA. Bekro Y-A. Anoubilé B. Defontaine A. Baratte B. Bach S. Rucheau S. Ravache M. Le Guével R. Corlu A. Bazureau J.-P. Med. Chem. Res. 2016; 25: 2940