N,N-Dialkyl-N’-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part X.* The First Pyrazolo[1,5-b][1,2,4,6]thiatriazine Derivatives and their Unusual Reactions with Acylating Agents
Rebecca E. Norman A , Michael V. Perkins A , Andris J. Liepa B and Craig L. Francis B C
+ Author Affiliations
- Author Affiliations
A School of Chemical and Physical Sciences, Flinders University, Bedford Park, SA 5042, Australia.
B CSIRO Materials Science and Engineering, Clayton, Vic. 3168, Australia.
C Corresponding author. Email: craig.francis@csiro.au
Australian Journal of Chemistry 66(11) 1323-1333 https://doi.org/10.1071/CH13282
Submitted: 1 June 2013 Accepted: 17 July 2013 Published: 16 September 2013
Abstract
N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent a regioselective reaction with 3-aminopyrazoles 2 to produce pyrazolo[1,5-b][1,2,4,6]thiatriazines 3, representatives of a new ring system. Attempted N-acylation of compounds 3 with acetic anhydride (or chloride) and benzoyl chloride in pyridine, only afforded 5-(pyridin-4-yl)-pyrazolo[1,5-b][1,2,4,6]thiatriazine derivatives 11. The analogous reaction with pyridazine led to the corresponding pyridazin-4-yl derivative.
References
[1] L. Yet, in Comprehensive Heterocyclic Chemistry III (Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), 2008, Vol. 4. pp. 1–141 (Elsevier: Oxford).[2] B. R. Buckley, in Comprehensive Heterocyclic Chemistry III (Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), 2008 Vol. 10. p. 431–491 (Elsevier: Oxford).
[3] F. F. Fleming, L. Yao, P. C. Ravikumar, L. Funk, B. C. Shook, J. Med. Chem. 2010, 53, 7902.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtV2kurvP&md5=5cfcea788e9864db9922a47a33b3fdb8CAS | 20804202PubMed |
[4] J. Elguero, in Comprehensive Heterocyclic Chemistry (Eds A. R. Katritzky, C. W. Rees) 1984, Vol. 5, pp. 167–303 (Pergamon: Oxford).
[5] R. Aggarwal, V. Kumar, R. Kumar, S. P. Singh, Beilstein J. Org. Chem. 2011, 7, 179.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXitlSnt7c%3D&md5=25e8f37b146684b607a23161181a337cCAS | 21448263PubMed |
[6] D. J. St. Jean, C. Fotsch, J. Med. Chem. 2012, 55, 6002.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XmtFWhsL0%3D&md5=f1320fb18aa6b80a4c7dcde9920ee852CAS | 22533875PubMed |
[7] D. K. Dalvie, A. S. Kalgutkar, S. C. Khojasteh-Bakht, R. S. Obach, J. P. O’Donnell, Chem. Res. Toxicol. 2002, 15, 269.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtVWrsLc%3D&md5=4b6f37fbe5faeb2ab6b5a9e916fd7517CAS | 11896674PubMed |
[8] C. M. Forsyth, C. L. Francis, S. Jahangiri, A. J. Liepa, M. V. Perkins, A. P. Young, Aust. J. Chem. 2010, 63, 659.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXksFSgtL0%3D&md5=84c1c8baac6806c58c3c14f94f1391b5CAS |
[9] S. A. S. Ghozlan, F. M. Abdelrazek, M. H. Mohamed, K. E. Azmy, J. Heterocycl. Chem. 2010, 47, 1379.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsV2hs77J&md5=9859f6d2127a14498e6bc919fd7c615cCAS |
[10] T. Cablewski, C. M. Forsyth, C. L. Francis, A. J. Liepa, V. Tran, Aust. J. Chem. 2008, 61, 785.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Siu7nF&md5=9840b7c4a25411a34416f24fccf2918cCAS |
[11] A. Akahane, H. Katayama, T. Mitsunaga, T. Kato, T. Kinoshita, Y. Kita, T. Kusunoki, T. Terai, K. Yoshida, Y. Shiokawa, J. Med. Chem. 1999, 42, 779.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXht1Sgsrs%3D&md5=163ef78678ee7b7fe12d343ac3f44071CAS | 10072675PubMed |
[12] B. A. Johns, K. S. Gudmundsson, S. H. Allen, Bioorg. Med. Chem. Lett. 2007, 17, 2858.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXkslyjsrg%3D&md5=fb2e3e549a6084e34223fbfba8c6942dCAS | 17350256PubMed |
[13] S. Follot, J. C. Debouzy, D. Crouzier, C. Enguehard-Gueiffier, A. Gueiffier, F. Nachon, B. Lefebvre, F. Fauvelle, Eur. J. Med. Chem. 2009, 44, 3509.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXoslGiu78%3D&md5=c8da50a5e079f7b075b0249d8db61e28CAS | 19185956PubMed |
[14] T. Cablewski, C. L. Francis, A. J. Liepa, Aust. J. Chem. 2008, 61, 332.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtFGgt7Y%3D&md5=93602f868f5946ee6a74ffe19b380fa9CAS |
[15] S. Shilcrat, I. Lantos, M. McGuire, L. Pridgen, L. Davis, D. Eggleston, D. Staiger, L. Webb, J. Heterocycl. Chem. 1993, 30, 1663.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXisVCqtro%3D&md5=fc07868a75b63a5c9d56e1f2dddf1457CAS |
[16] D. M. Volochnyuk, A. N. Kostyuk, A. M. Pinchuk, A. A. Tolmachev, Tetrahedron Lett. 2003, 44, 391.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XpsVemtrk%3D&md5=1de6945fd4fc3b259e9d16d96a075bcbCAS |
[17] G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=c16dcfe329fce2375df65b1474a83185CAS | 18156677PubMed |
[18] L. J. Barbour, J. Supramol. Chem. 2001, 1, 189.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXitlOlsb8%3D&md5=83d3d27f6ab0b644a196d2fa998350feCAS |
