Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides

Tetrahedron

Volumn 66, Issue 24, 2010, Pages 4330-4338

  Konstantinova, Lidia S ^a   Bol'shakov, Oleg I ^a   Obruchnikova, Natalia V ^a   Golova, Svetlana P ^a   Nelyubina, Yulia V ^b   Lyssenko, Konstantin A ^b   Rakitin, Oleg A ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

1,2,5 Thiadiazoles; 2 Iminothioacetamides; 2 Oxoacetamides; 2H 1,2,3 Dithiazoles; Primary amines; Secondary amines; Sulfur nitrogen heterocycles

Indexed keywords

2 OXOACETAMIDE; ACETAMIDE; ACETAMIDE DERIVATIVE; ALIPHATIC AMINE; AMINE; BENZYLAMINE; DIMETHYL SULFOXIDE; IMINO ACID; SULFUR; TETRAHYDROFURAN; THIADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; THIOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; ELECTRON; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 77953607058     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.033     Document Type: Article

References (28)

1. Khmelnitsky L.I., and Rakitin O.A. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Pergamon, Oxford 433-452 Chapter 4.11
2. Rakitin O.A. In: Katritzky A.R., Ramsden C.A., Scriven E.F.V., and Taylor R.J.K. (Eds). Comprehensive Heterocyclic Chemistry III Vol. 6 (2008), Elsevier, Oxford 1-36 Chapter 6.01
3. Appel R., Janssen H., Siray M., and Knoch F. Chem. Ber. 118 (1985) 1632-1643
4. Lee H., and Kim K. J. Org. Chem. 58 (1993) 7001-7008
5. Lee H.-S., and Kim K. Tetrahedron Lett. 37 (1996) 3709-3712
6. Chang Y.-G., Lee H.-S., and Kim K. Tetrahedron Lett. 42 (2001) 8197-8200
7. Jeon M.-K., and Kim K. J. Chem. Soc., Perkin Trans. 1 (2000) 3107-3112
8. Gray M.A., Rees C.W., and Williams D.J. Heterocycles 37 (1994) 1827-1851
9. Emayan K., and Rees C.W. Bull. Soc. Chim. Belg. 106 (1997) 605-611
10. Konstantinova L.S., Bol'shakov O.I., Obruchnikova N.V., Laborie H., Tonga A., Sopéna V., Lanneluc I., Picot L., Sablé S., Thiéry V., and Rakitin O.A. Bioorg. Med. Chem. Lett. 19 (2009) 136-141
11. Konstantinova L.S., Bol'shakov O.I., Obruchnikova N.V., Golova S.P., Nelyubina Y.V., Lyssenko K.A., and Rakitin O.A. Mendeleev Commun. (2009) 84-86
12. Bader R.F.W. Atoms in Molecules. A Quantum Theory (1990), Clarendron, Oxford
13. Espinosa E., Molins E., and Lecomte C. Chem. Phys. Lett. 285 (1998) 170-173
14. Espinosa E., Alkorta I., Rozas I., Elguero J., and Molins E. Chem. Phys. Lett. 336 (2001) 457-461
15. Masuda K., Adachi J., and Nomura K. J. Chem. Soc., Perkin Trans. 1 (1981) 1033-1036
16. Goldish D., Axon B.W., and Moore H.W. Heterocycles 2 (1983) 187-192
17. Lunn W.H.W., and Shadle J.K. Tetrahedron 48 (1992) 8615-8620
18. Ross J.M., and Smith W.C. J. Amer. Chem. Soc. 86 (1964) 2861-2868
19. Maliverney C., and Viehe H.G. Tetrahedron Lett. 44 (1990) 6339-6342
20. Choi S.-H., and Kim K. Tetrahedron 52 (1996) 8413-8438
21. Venkatraman S., Bogen S.L., Arasappan A., Bennett F., Chen K., Jao E., Liu Y.-T., Lovey R., Hendrata S., Huang Y., Pan W., Parekh T., Pinto P., Popov V., Pike R., Ruan S., Santhanam B., Vibulbhan B., Wu W., Yang W., Kong J., Liang X., Wong J., Liu R., Butkiewicz N., Chase R., Hart A., Agrawal S., Ingravallo P., Pichardo J., Kong R., Baroudy B., Malcolm B., Guo Z., Prongay A., Madison V., Broske L., Cui X., Cheng K.-C., Hsieh Y., Brisson J.-M., Prelusky D., Korfmacher W., White R., Bogdanowich-Knipp S., Pavlovsky A., Bradley P., Saksena A.K., Ganguly A., Piwinski J., Girijavallabhan V., and Njoroge F.G. J. Med. Chem. 49 (2006) 6074-6086
22. Dhar T.G.M., Wrobleski S.T., Lin S., Furch J.A., Nirschl D.S., Fan Y., Todderud G., Pitt S., Doweyko A.M., Sack J.S., Mathur A., McKinnon M., Barrish J.C., Dodd J.H., Schieven G.L., and Leftheris K. Bioorg. Med. Chem. Lett. 17 (2007) 5019-5024
23. Summa V., Petrocchi A., Bonelli F., Crescenzi B., Donghi M., Ferrara M., Fiore F., Gardelli C., Paz O.G., Hazuda D.J., Jones P., Kinzel O., Laufer R., Monteagudo E., Muraglia E., Nizi E., Orvieto F., Pace P., Pescatore G., Scarpelli R., Stillmock K., Witmer M.V., and Rowley M. J. Med. Chem. 51 (2008) 5843-5855
24. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T.A., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe, Gill M.P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A.9 (1998), Gaussian, Pittsburgh, PA
25. AIM2000 designed by Friedrich Biegler-König, University of Applied Sciences, Bielefeld, Germany.
26. Coppola G.M., and Damon R.E. J. Heterocycl. Chem. 32 (1995) 1133-1139
27. Matsumoto K., Hashimoto S., Uchida T., Okamoto T., and Otani S. Chem. Ber. 122 (1989) 1357-1364
28. Campaigne E., Skowronski G., and Rogers R.B. Synth. Commun. 3 (1973) 325-332