A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines

References

• (a) Henry, R. J. Bacteriol. Rev. 1943, 7, 175–262. doi:10.1128/MMBR.7.4.175-262.1943
   PubMedGoogle Scholar
  (b) Vandi, A.; Moeller, T.; Audrieth, L. F. J. Org. Chem. 1961, 26, 1136–1138. DOI: 10.1021/jo01063a039.
   Web of Science ®Google Scholar
  (c) Supuran, C. T. Molecules 2017, 22, 1642–1646. DOI: 10.3390/molecules22101642.
   Web of Science ®Google Scholar
  (d) Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. T. Curr. Med. Chem. 2003, 10, 925–953. DOI: 10.2174/0929867033457647.
   PubMed Web of Science ®Google Scholar
  (e) Maren, T. H. Annu. Rev. Pharmacol. Toxicol. 1976, 16, 309–327. DOI: 10.1146/annurev.pa.16.040176.001521.
   PubMed Web of Science ®Google Scholar
• Das, T. C.; Quadri, S. A.; Farooqui, M. Chem. Biol. Interface 2018, 8, 194–204.
   Google Scholar
• (a) Vega, J. A.; Alajarin, R.; Vaquero, J. J.; Alvarez-Builla, J. Tetrahedron 1998, 54, 3589–3606. DOI: 10.1016/S0040-4020(98)00093-3.
   Web of Science ®Google Scholar
  (b) Kolosov, M. A.; Al-Ogaili, M. J. K.; Kulyk, O. G.; Orlov, V. D. Chem. Heterocycl. Comp. 2015, 51, 691–694. DOI: 10.1007/s10593-015-1759-5.
   Web of Science ®Google Scholar
  (c) Han, W.; Hu, Z. US Patent Publication No WO/2007/027454, 2007.
   Google Scholar
• (a) Kappe, СO. Molecules 1998, 3, 1–9. DOI: 10.3390/30100001.
   Web of Science ®Google Scholar
  (b) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043–1052. DOI: 10.1016/S0223-5234(00)01189-2.
   PubMed Web of Science ®Google Scholar
  (c) Sandhu, J. S.; Sandhu, S. S. Arkivoc 2012, 1, 66–133.
   Google Scholar
• (a) Edraki, N.; Mehdipour, A. R.; Khoshneviszadeh, M.; Miri, R. Drug Discov. Today 2009, 14, 1058–1066. DOI: 10.1016/j.drudis.2009.08.004.
   PubMed Web of Science ®Google Scholar
  (b) Hilgeroth, A. Mini Rev. Med. Chem. 2002, 2, 235–245. 2, DOI: 10.2174/1389557023406241.
   PubMed Web of Science ®Google Scholar
  (c) Velena, A.; Zarkovic, N.; Troselj, K. G.; Bisenieks, E.; Krauze, A.; Poikans, J.; Duburs, G. Oxid. Med. Cell. Longevity 2016, 2016, 1–35. DOI: 10.1155/2016/1892412.
   Google Scholar
• (a) Hassan, A. Y.; Sarg, M. T.; Bayoumi, A. H.; El-Deeb, M. A. J. Heterocyclic Chem. 2018, 55, 1450–1478. DOI: 10.1002/jhet.3184.
   Web of Science ®Google Scholar
  (b) Battaglia, U.; Moody, C. J. J. Nat. Prod. 2010, 73, 1938–1939. DOI: 10.1021/np100298m.
   PubMed Web of Science ®Google Scholar
  (c) Oukoloff, K.; Lucero, B.; Francisco, K. R.; Brunden, K. R.; Ballatore, C. Eur. J. Med. Chem. 2019, 165, 332–346. DOI: 10.1016/j.ejmech.2019.01.027.
   PubMed Web of Science ®Google Scholar
• (a) Orlov, V. D.; Desenko, S. M.; Potekhin, K. A.; Struchkov, Y. T. Chem. Heterocycl. Compd. 1988, 24, 192–196. DOI: 10.1007/BF00473331.
   Google Scholar
  (b) Desenko, S. M.; Komykhov, S. A.; Orlov, V. D.; Meier, H. J. Heterocycl. Chem. 1998, 35, 989–990. DOI: 10.1002/jhet.5570350434.
   Web of Science ®Google Scholar
  (c) Rudenko, R. V.; Komykhov, S. A.; Musatov, V. I.; Desenko, S. M. J. Heterocycl. Chem. 2009, 46, 285–288. DOI: 10.1002/jhet.81.
   Web of Science ®Google Scholar
  (d) Chebanov, V. A.; Gura, K. A.; Desenko, S. M. Top. Heterocycl. Chem. 2010, 23, 41–84. doi:10.1007/978-3-642-12675-8.
   Google Scholar
  (e) Chebanov, V. A.; Desenko, S. M.; Gurley, T. W. Azaheterocycles Based on α,β-Unsaturated Carbonyls; Springer-Verlag Berlin Heidelberg: Berlin, 2008; pp 61–147.
   Google Scholar
• (a) Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 1946, 39–45. DOI: 10.1039/jr9460000039.
   Google Scholar
  (b) Curtis, R. G.; Heilbron, I.; Jones, E. R. H.; Wood, G. F. J. Chem. Soc. 1953, 1953, 457–464. DOI: 10.1039/jr9530000457.
   Google Scholar
• (a) Barber, M.; Bordoli, R. S.; Sedgwick, R. D.; Tyler, A. N. J. Chem. Soc, Chem. Commun. 1981, 1981, 325–327. DOI: 10.1039/c39810000325.
   Google Scholar
  (b) Barber, M.; Bordoli, R. S.; Elliot, G. J.; Sedgwick, R. D.; Tyler, A. N. Anal. Chem. 1982, 54, 645–657. DOI: 10.1021/ac00241a002.
   Web of Science ®Google Scholar
• (a) Sedash, Y. V.; Gorobets, N. Y.; Chebanov, V. A.; Konovalova, I. S.; Shishkin, O. V.; Desenko, S. M. RSC Adv. 2012, 2, 6719–6728. DOI: 10.1039/c2ra20195j.
   Web of Science ®Google Scholar
  (b) Gorobets, N. Y.; Sedash, Y. V.; Ostras, K. S.; Zaremba, O. V.; Shishkina, S. V.; Baumer, V. N.; Shishkin, O. V.; Kovalenko, S. M.; Desenko, S. M.; Van der Eycken, E. V. Tetrahedron Lett. 2010, 51, 2095–2098. DOI: 10.1016/j.tetlet.2010.02.045.
   Web of Science ®Google Scholar
  (c) El Ashry, E. S. H.; Rashed, N. Adv. Heterocycl. Chem. 1998, 72, 127–224. doi:10.1016/S0065-2725(08)60316-5
   Web of Science ®Google Scholar
• Gladkov, E. S.; Chebanov, V. A.; Desenko, S. M.; Shishkin, O. V.; Shishkina, S. V.; Dallinger, D.; Kappe, C. O. Heterocycles 2007, 73, 469–480.
   Web of Science ®Google Scholar