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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Thiophene Ring-Opening Reactions V. Expedient Synthesis of 1,3,4- Thiadiazoline-Sulfanyl[1,3]thiazin-4-one Hybrids

Author(s): Abdullah K. Jarrar, Mustafa M. El-Abadelah*, Salim S. Sabri, Jalal A. Zahra* and Mohammad S. Hamdan

Volume 19, Issue 11, 2022

Published on: 29 April, 2022

Page: [976 - 982] Pages: 7

DOI: 10.2174/1570178619666220314151114

Price: $65

Abstract

The preparation of 6-chloro-5-nitrothieno[3,2-e][1,3]thiazin-4-one incorporating 2-(Nmorpholinyl) moiety is achieved via a conventional route. Interaction of the latter substrate with a set of N'-(aryl) benzothiohydrazides 1a-f, in the presence of triethylamine, led to a thiophene ring-opening process with the consequent generation of the respective thiolate salts 8a-f. Alkylation of the latter, using methyl iodide or allyl chloride, generated the respective novel 1,3,4-thiadiazoline–6-sulfanyl-1,3- thiazin-4-one hybrids, the structures of which were verified by HRMS and NMR spectral data.

Keywords: N'-(Aryl)benzothiohydrazides, chalcogen bond, formal [4+1] annulation, thieno[3, 2-e][1, 3]thiazin-4-one, S-allylation, β-nitrothiophenes.

Graphical Abstract

[1]
Guanti, G.; Dell’Erba, C.; Leandri, G.; Thea, S. J. Chem. Soc., Perkin Trans. 1, 1974, 2357–2360, 2357.
[http://dx.doi.org/10.1039/p19740002357]
[2]
Surange, S.S.; Kumaran, G.; Rajappa, S.; Rajalakshmi, K.; Pattabhi, V. Tetrahedron, 1997, 53(25), 8531-8540.
[http://dx.doi.org/10.1016/S0040-4020(97)00511-5]
[3]
Dell’Erba, C.; Gabellini, A.; Novi, M.; Petrillo, G.; Tavani, C.; Cosimelli, B.; Spinelli, D. Tetrahedron, 2001, 57(38), 8159-8165.
[http://dx.doi.org/10.1016/S0040-4020(01)00765-7]
[4]
Surange, S.S.; Rajappa, S. Tetrahedron Lett., 1998, 39(39), 7169-7172.
[http://dx.doi.org/10.1016/S0040-4039(98)01535-4]
[5]
Dell’Erba, C.; Spinelli, D.; Leandri, G. J. Chem. Soc. D, 1969, 549(10), 549.
[http://dx.doi.org/10.1039/c29690000549]
[6]
Dell’Erba, C.; Mele, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron Lett., 1990, 31(34), 4933-4936.
[http://dx.doi.org/10.1016/S0040-4039(00)97773-6]
[7]
Bianchi, L.; Dell’Erba, C.; Maccagno, M.; Morganti, S.; Petrillo, G.; Rizzato, E.; Sancassan, F.; Severi, E.; Spinelli, D.; Tavani, C. ARKIVOC, 2006, 169-185.
[http://dx.doi.org/10.3998/ark.5550190.0007.714]
[8]
Abadleh, M.M.; Abdullah, A.H.; Awwadi, F.F.; El-Abadelah, M.M. Tetrahedron, 2021, 83, 131957.
[http://dx.doi.org/10.1016/j.tet.2021.131957]
[9]
Abdullah, A.H.; El-Abadelah, M.M.; Zahra, J.A.; Sabri, S.S.; Awwadi, F.F. Monatsh. Chem., 2021, 152(7), 853-862.
[http://dx.doi.org/10.1007/s00706-021-02798-4]
[10]
Chen, J.R.; Hu, X.Q.; Lu, L.Q.; Xiao, W. J. Chem. Rev., 2015, 115(11), 5301-5365.
[http://dx.doi.org/10.1021/cr5006974] [PMID: 25992465]
[11]
Abu-El-Halawa, R.; Sarabi, A.; El-Abadelah, M.M. Monatsh. Chem., 2008, 139(10), 1251-1255.
[http://dx.doi.org/10.1007/s00706-008-0920-6]
[12]
Mueller, J.L.; Gibson, M.S.; Hartman, J.S. Can. J. Chem., 1996, 74(7), 1329-1334.
[http://dx.doi.org/10.1139/v96-148]
[13]
Mohammad, T.; Gibson, M.S. Phosphorus Sulfur Silicon Relat. Elem., 1992, 70(1), 243-253.
[http://dx.doi.org/10.1080/10426509208049173]
[14]
Pandya, N.; Basile, A.J.; Gupta, A.K.; Hand, P.; Maclaurin, C.L.; Mohammad, T.; Ratemi, E.S.; Gibson, M.S.; Richardson, M.F. Can. J. Chem., 1993, 71(4), 561-571.
[http://dx.doi.org/10.1139/v93-078]
[15]
Nguyen, H.M.; Graber, C.J. Int. J. Antimicrob. Agents, 2020, 56(4), 106085.
[http://dx.doi.org/10.1016/j.ijantimicag.2020.106085] [PMID: 32659466]
[16]
Caprile, K.A. J. Vet. Pharmacol. Ther., 1988, 11, 1-32.
[http://dx.doi.org/10.1111/j.1365-2885.1988.tb00117.x]
[17]
Goerdeler, J.; Tiedt, M-L.; Nandi, K. Chem. Ber., 1981, 114(8), 2713-2722.
[http://dx.doi.org/10.1002/cber.19811140805]
[18]
Yokoyama, M.; Sawachi, Y.; Isso, T. J. Org. Chem., 1973, 38(4), 802-804.
[http://dx.doi.org/10.1021/jo00944a038]
[19]
Yokoyama, M.; Sato, K.; Tateno, H.; Hatanaka, H. J. Chem. Soc., Perkin Trans. 1, 1987, I, 623-628.
[http://dx.doi.org/10.1039/p19870000623]
[20]
Martin, D.; Gelbin, M. Z. Chem., 1985, 25(12), 430-431.
[http://dx.doi.org/10.1002/zfch.19850251205]
[21]
El-Shaieb, K.M.; Abdel-Latif, F.F.; El-Din, A.G. J. Chem. Res., 2012, 36(5), 308-311.
[http://dx.doi.org/10.3184/174751912X13345902079361]
[22]
Seitz, T.; Fu, P.; Haut, F.L.; Adam, L.; Habicht, M.; Lentz, D.; MacMillan, J.B.; Christmann, M. Org. Lett., 2016, 18(13), 3070-3073.
[http://dx.doi.org/10.1021/acs.orglett.6b01166] [PMID: 27286418]
[23]
Azab, M.E.; Youssef, M.M.; El-Bordany, E.A. Molecules, 2013, 18(1), 832-844.
[http://dx.doi.org/10.3390/molecules18010832] [PMID: 23344196]
[24]
Winterfeldt, E.; Nelke, J.M. Chem. Ber., 1967, 100(11), 3671-3678.
[http://dx.doi.org/10.1002/cber.19671001123]
[25]
Simchen, G.; Entenmann, G. Justus Liebigs Ann. Chem., 1977, 1977(8), 1249-1266.
[http://dx.doi.org/10.1002/jlac.197719770802]
[26]
Gilkerson, T.; Jennens, D.C.; Coombs, M.E. European Patent, EP245901 A2, 1987.
[27]
Warrener, R.N.; Cain, E.N. Chem. Ind., 1964, 1989-1990.
[28]
Cain, E.N.; Warrener, R.N. Aust. J. Chem., 1970, 23(1), 51-72.
[http://dx.doi.org/10.1071/CH9700051]
[29]
Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem. Lett., 2002, 12(12), 1551-1557.
[http://dx.doi.org/10.1016/S0960-894X(02)00252-4] [PMID: 12039560]
[30]
Li, Y.; Geng, J.; Liu, Y.; Yu, S.; Zhao, G. ChemMedChem, 2013, 8(1), 27-41.
[http://dx.doi.org/10.1002/cmdc.201200355] [PMID: 23208773]
[31]
Hu, Y.; Li, C.Y.; Wang, X.M.; Yang, Y.H.; Zhu, H.L. Chem. Rev., 2014, 114(10), 5572-5610.
[http://dx.doi.org/10.1021/cr400131u] [PMID: 24716666]
[32]
Haider, S.; Alam, M.S.; Hamid, H. Eur. J. Med. Chem., 2015, 92, 156-177.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.035] [PMID: 25553540]
[33]
Jensen, K.A.; Miquel, L.F. Acta Chem. Scand., 1952, 6, 189-194.
[http://dx.doi.org/10.3891/acta.chem.scand.06-0189]
[34]
Holmberg, B. Ark. Kemi, 1954, 7, 529-534.
[35]
Scherowsky, G. Tetrahedron Lett., 1971, 1(52), 4985-4988.
[http://dx.doi.org/10.1016/S0040-4039(01)97606-3]
[36]
Abadleh, M.M.; Arafat, T.; Abu-qatouseh, L.; El-abadelah, M.M.; Voelter, W. Z. Naturforsch. B. J. Chem. Sci., 2019, 74b(6), 507-512.
[http://dx.doi.org/10.1515/znb-2019-0023]

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