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Synthesis 2016; 48(18): 3134-3140
DOI: 10.1055/s-0035-1562133
DOI: 10.1055/s-0035-1562133
paper
(Hex-2-en-ylidene)-N-Substituted Hydrazinecarbothioamides and 2,3-Dichloro-1,4-naphthoquinone: Nucleophilic Substitution Reactions and Synthesis of Naphtho[2,3-f][1,3,4]thiadiazepines and Naphtho[2,3-d]thiazoles
Further Information
Publication History
Received: 19 January 2016
Accepted after revision: 29 March 2016
Publication Date:
10 May 2016 (online)
Abstract
The coupling reaction between N-substituted (E)-hex-2-en-ylidene hydrazinecarbothioamides and 2,3-dichloro-1,4-naphthoquinone affords substituted amino-5-pentenyl-naphtho[2,3-f]-1,3,4-thiadiazepine-6,11-diones and 2-(substituted amino)naphtho[2,3-d]thiazole-4,9-diones. These conversions can be rationalized by proposing a nucleophilic addition to C2 and C3 of dichloro-1,4-naphthoquinone. The structure of one of the products was confirmed by single-crystal X-ray analysis.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562133.
- Supporting Information
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References
- 1 Hassan AA, Ibrahim YR, Shawky AM. J. Heterocycl. Chem. 2010; 47: 118
- 2 Khalafy J, Mohammadlou M, Mahmoody M, Salami F, Marjani AP. Tetrahedron Lett. 2015; 56: 1528
- 3 Al-Alshaikh MA, Lahsasni SA. Asian J. Chem. 2013; 25: 10199
- 4 Hassan AA, Ibrahim YR, Shawky AM. J. Sulfur Chem. 2007; 28: 211
- 5 Hassan AA, Refaey SM, Shehatta HS. ARKIVOC 2007; (xv): 265
- 6 Ryu C.-K, Choi KU, Shim J.-Y, You H.-J, Choi IH, Chae MJ. Bioorg. Med. Chem. 2003; 11: 4003
- 7 Huang S.-T, Kuo H.-S, Hsiao C.-L, Lin Y.-L. Bioorg. Med. Chem. 2002; 10: 1947
- 8 Tandon VK, Chhor RB, Singh RV, Rai S, Yadav DB. Bioorg. Med. Chem. Lett. 2004; 14: 1079
- 9 Tandon VK, Singh RV, Yadav DB. Bioorg. Med. Chem. Lett. 2004; 14: 2901
- 10 Principles of Chemotherapy and Pharmacology, In Comprehensive Medicinal Chemistry II . Donawho CK, Shoemaker AR, Palma JP, Triggle D, Taylor J. Elsevier; Amsterdam: 2006: 33-53
- 11 Perkins WE, Schroeder RL, Carrano RA, Imondi AR. Cancer Treat. Rep. 1984; 68: 841; http://www.ncbi.nlm.nih.gov/ pubmed/16733698
- 12 Selassie CD, Ttansch C, Khwaja TA. J. Med. Chem. 1990; 33: 1914
- 13 Krapcho AP, Menta E, Oliva A, Di Domenico R, Fiocchi L, Maresch ME, Gallagher CE, Hacker MP, Beggiolin G, Giuliani FC, Pezzoni G, Spinelli S. J. Med. Chem. 1998; 41: 5429
- 14 Gomez-Monterrey I, Santelli G, Campiglia P, Califano D, Falasconi F, Pisano C, Vesci L, Lama T, Grieco P, Novellino E. J. Med. Chem. 2005; 48: 1152
- 15 Khalil MA, Habib NS. Arch. Pharm. (Weinheim, Ger.) 1990; 323: 471
- 16 Khalil MA, El-Sayed QA, El-Shamy HA. Arch. Pharm. (Weinheim, Ger.) 1993; 326: 489
- 17 Kidwai M, Sapra P, Misra P, Saxena RK, Singh M. Bioorg. Med. Chem. 2001; 9: 217
- 18 Harikrishna S, Ravindranath LK. J. Appl. Chem. 2015; 4: 99
- 19 Li Z, Yang Q, Qian X. Bioorg. Med. Chem. 2005; 13: 3149
- 20 Russowsky D, Neto BA. D. Tetrahedron Lett. 2004; 45: 1437
- 21 Kodouri ND, Hileman B, Cox JD, Scott H, Hoang P, Robbins A, Bowers K, Tsebaot L, Miao K, Castaneda M, Coffin M, Wei G, Claridge TD. W, Roberts KP, Hussaini SR. RSC Adv. 2013; 3: 181
- 22 Guzaev AP. Tetrahedron Lett. 2011; 52: 434
- 23 Pettersson B, Hasimbegovic V, Bergman J. J. Org. Chem. 2011; 76: 1554
- 24 Hassan AA, Abdel-Latif FF, Nour El-DinA. M, Mostafa SM, Nieger M, Bräse S. Tetrahedron 2012; 68: 8487
- 25 Brehme R, Klemann A. Tetrahedron 1987; 43: 4113
- 26 Endes D, Syrig R, Raabe G, Fernández R, Gasch C, Lassaletta JM, Llera JM. Synthesis 1996; 48
- 27 Díez E, Fernández R, Gasch C, Lassaletta JM, Llera JM, Martin-Zamora E, Vázquez J. J. Org. Chem. 1997; 62: 5144
- 28 Neto BA. D, Lapis AA. M, Bernd AB, Russowsky D. Tetrahedron 2009; 65: 2484
- 29 Ireland RE, Brown FR. J. Org. Chem. 1980; 45: 1868
- 30 Hassan AA, Nour El-DinA. M, Abdel-latif FF, Mostafa SM, Bräse S. Chem. Pap. 2012; 66: 295
- 31 Hassan AA, Aly AA, El-Shaieb KM. A, Bedair TM. I, Bräse S, Brown AB. J. Heterocycl. Chem. 2014; 51: 674
- 32 Boutherin-Falson O, Desquand-Billiald S, Favrou A, Finet M, Tembo O, Torregrosa J.-L, Yannic-Arnoult S, Domagala-Le Marquer F. US Patent 6,262,095B1, 2001
- 33 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008; 64: 112
- 34 Crystallographic data (excluding structure factors) for the structure reported in this work have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-1407257 (4b) and CCDC-1407504 (4b_polymorph). These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk).