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Synthesis 2025; 57(10): 1755-1761
DOI: 10.1055/a-2538-6958
DOI: 10.1055/a-2538-6958
paper
An Unexpected Synthesis of 2,3-Bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones and Their Cyclocondensation with Hydrazine for the Synthesis of 4,5-Bis(methylthio)-3,6-di(het)arylpyridazines
K.M. thanks DBT Glue (Grant No. BT/PR23078/MED/29/1253/2017 dated 22-03-2018) and VGST Project (Grant No. Ksteps/VGST/GRD-681/KFIST(L1)/2018 dated 27-08-2018) for financial support.
Dedicated to Prof. K. S. Rangappa on the occasion of his 70th birthday.
Abstract
An unexpected formation of novel 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones is reported, when methyl ketones are reacted with α-oxodithioesters in the presence of sodium hydride in DMF followed by treatment with methyl iodide. A potential application of these key intermediates for the synthesis of unreported 4,5-bis(methylthio)-3,6-di(het)arylpyridazines is explored by reacting them with hydrazine in the presence of potassium hydroxide in isopropyl alcohol. Possible mechanisms for the formation of 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones and 4,5-bis(methylthio)-3,6-di(het)arylpyridazines are proposed.
Key words
hydrazine - pyridazine - 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones - cyclocondensation - unexpectedSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2538-6958.
- Supporting Information
Publikationsverlauf
Eingereicht: 31. Dezember 2024
Angenommen nach Revision: 13. Februar 2025
Accepted Manuscript online:
13. Februar 2025
Artikel online veröffentlicht:
19. März 2025
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References
- 1 Benson SC, Palabrica CA, Snyder JK. J. Org. Chem. 1987; 52: 4610
- 2 Rohet F, Rubat C, Coudert P, Couquelet J. Bioorg. Med. Chem. 1997; 5: 655
- 3 Tucker JA, Allwine DA, Grega KC, Barbachyn MR, Klock JL, Adamski JL, Brickner SJ, Hutchinson DK, Ford CW, Zurenko GE, Conradi RA, Burton PS, Jensen RM. J. Med. Chem. 1998; 41: 3727
- 4 Liu Z-Q, Zhang Q, Liu Y-L, Yu X-Q, Chui R-H, Zhang L-L, Zhao B, Ma L-Y. Bioorg. Med. Chem. 2024; 111: 117847
- 5 Hassan MS. A, Ahmed EM, El-Malah AA, Kassab AE. Arch. Pharm. (Weinheim) 2022; 355: 2200067
- 6 Johnsen M, Rehse K, Pertz H, Stasch JP, Bischoff E. Arch. Pharm. (Weinheim) 2003; 336: 591
- 7 Tsuji T, Yamaguchi M, Kuroyanagi J, Furuzono S, Konishi M, Terayama K, Tanaka J, Saito M, Kobayashi Y. Bioorg. Med. Chem. Lett. 2019; 29: 1785
- 8 Yu M, Ledeboer MW, Daniels M, Malojcic G, Tibbitts TT, Gal MC, Pan-Zhou X-R, Westerling-Bui A, Beconi M, Reilly JF, Mundel P, Harmange J-C. ACS Med. Chem. Lett. 2019; 10: 1579
- 9 Ye C, Xu R, Cao Z, Song Q, Yu G, Shi Y, Liu Z, Liu X, Deng Y. Bioorg. Chem. 2021; 111: 104895
- 10 Qian H-Y, Wang Z-L, Xie X-Y, Pan Y-L, Li G-J, Xie X, Chen J-Z. Eur. J. Med. Chem. 2017; 137: 598
- 11 Lewis RT, Blackby WP, Blackbum T, Jennings AS. R, Pike A, Wilson RA, Hallett DJ, Cook SM, Ferris P, Marshall GR, Reynolds DS, Sheppard WF. A, Smith AJ, Sohal B, Stanley J, Tye SJ, Wafford KA, Atack JR. J. Med. Chem. 2006; 49: 2600
- 12 Rival Y, Hoffmann R, Didier B, Rybaltchenko V, Bourguignon J.-J, Wermuth CG. J. Med. Chem. 1998; 41: 311
- 13 Minetto G, Lampariello LR, Taddei M. Synlett 2005; 2743
- 14 Attanasi OA, Favi G, Filippone P, Perrulli FR, Santeusanio S. Org. Lett. 2009; 11: 309
- 15 Al Dulayymi AR, Baird MS. Tetrahedron 1998; 54: 12897
- 16 Hamasaki A, Ducray R, Boger DL. J. Org. Chem. 2006; 71: 185
- 17 Rykowski A, Woliñska E. Tetrahedron Lett. 1996; 37: 5795
- 18 Schnell SD, González JA, Sklyaruk J, Linden A, Gademann K. J. Org. Chem. 2021; 86: 12008
- 19 Kodama T, Sasaki I, Sugimura H. J. Org. Chem. 2021; 86: 8926
- 20 Zhang J, Zhang H, Wang Z, Yao W. Synthesis 2024; 56: 3915
- 21 Wu L, Yang Y, Gao M, Zhang D, Shu W, Zhu Y, Wu A. Synlett 2012; 23: 2137
- 22 Yang Y, Gao M, Wu L-M, Deng C, Zhang D-X, Gao Y, Zhu Y-P, Wu A-X. Tetrahedron 2011; 67: 5142
- 23 Yin G, Wang Z, Chen A, Gao M, Wu A, Pan Y. J. Org. Chem. 2008; 73: 3377
- 24 Zhang D, Yang Y, Gao M, Shu W, Wu L, Zhu Y, Wu A. Tetrahedron 2013; 69: 1849
- 25 Cheruku S, Sajith AM, Narayana Y, Shetty P, Nagarakere SC, Sagar KS, Manikyanally KN, Rangappa KS, Mantelingu K. J. Org. Chem. 2021; 86: 5530
- 26 Ramesha AB, Pavan Kumar CS, Sandhya NC, Kumara MN, Mantelingu K, Rangappa KS. RSC Adv. 2016; 6: 48375
- 27 Swarup HA, Kemparajegowda, Mantelingu K, Rangappa KS. ChemistrySelect 2018; 3: 703
- 28 Shamanth S, Chaitra N, Gurukiran M, Mamatha M, Lokanath NK, Rangappa KS, Mantelingu K. Org.Biomol.Chem. 2020; 18: 2678
- 29 Gopinatha VK, Swarup HA, Raghavan SC, Mantelingu K, Rangappa KS. Synlett 2019; 30: 2004
- 30 Swaroop TR, Rangappa KS, Torun L. ChemistrySelect 2021; 6: 177
- 31 Swaroop TR, Wang Z.-Q, Li QY, Wang H.-S. J. Electrochem. Soc. 2020; 167: 046504
- 32 Suresh RN, Swaroop TR, Gowda D, Mantelingu K, Rangappa KS. RSC Adv. 2023; 13: 4910
- 33 Kiran KR, Swaroop TR, Rajeev N, Anil SM, Rangappa KS, Sadashiva MP. Synthesis 2020; 52: 1444
- 34 Suresh RN, Swaroop TR, Shalini V, Mantelingu K, Rangappa KS. Tetrahedron Lett. 2023; 116: 154302
- 35 Shivaraj M, Suresh RN, Swaroop TR, Kumara MN, Rangappa KS, Mantelingu K, Mamatha Devi AB, Manasa MP, Umashankara M. Electrochemistry 2023; 91: 122001
- 36 Kiran KR, Swaroop TR, Preetham R, Georghiou PE, Rangappa KS, Sadashiva MP. ChemistrySelect 2023; 8: e202203618
- 37 Kiran KR, Swaroop TR, Santhosh C, Rangappa KS, Sadashiva MP. ChemistrySelect 2021; 6: 7262
- 38 Kiran KR, Swaroop TR, Sukrutha KP, Shruthi JB, Anil SM, Rangappa KS, Sadashiva MP. Synthesis 2019; 51: 4205
- 39 Kavya K, Sahana M, Swaroop TR, Sridhar BT, Mantelingu K. Tetrahedron Lett. 2025; 155: 155418
- 40 Honnabandar KV, Suresh RN, Kavya K, Swaroop TR, Rangappa KS, Mantelingu K. Synlett 2024; 35: in press
- 41 Kavya K, Honnabandar KV, Sridhar BT, Swaroop TR, Mantelingu K. New J. Chem. 2024; 48: 17998