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Original Articles

Isothiocyanates in Heterocyclic Synthesis

Satyavan Sharma Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, 226 001, India
Pages 327-454 | Received 18 Dec 1987, Published online: 05 Oct 2006

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Amira A. El-Sayed, Galal A. Elsayed, Sameh A. Rizk & Mahmoud F. Ismail. (2024) Synthesis, Insecticidal Activity and DFT Study of 1,2,4-Triazolidinthione, 1,3,5-Oxadiazine and Thiourea Derivatives. Organic Preparations and Procedures International 56:1, pages 38-51.
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Sergey A. Popov, Zhiwen Qi, Chengzhang Wang & Elvira E. Shults. (2023) Synthesis of ursane-derived isothiocyanates and study of their reactions with series of amines and ammonia. Journal of Sulfur Chemistry 44:5, pages 523-541.
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Manasa Kadagathur, Dilep Kumar Sigalapalli, Sandip Patra & Neelima D. Tangellamudi. (2021) Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization. Synthetic Communications 51:14, pages 2213-2224.
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Ibrahim F. Nassar, Saad R. Att-Allah & Magdy M. Hemdan. (2018) Utility of thiophene-2-carbonyl isothiocyanate as a precursor for the synthesis of 1,2,4-triazole, 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives with evaluation of their antitumor and antimicrobial activities. Phosphorus, Sulfur, and Silicon and the Related Elements 193:10, pages 630-636.
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A.F. Fahmy, N. Ali, H. Abdelhamid, S. Shiba & M.M. Hemdan. (2010) The Utility of p-N-Succinimidobenzoyl Isothiocyanate in Synthesis of Benzoxazole, Quinazoline, Pyrimidine, 1,2,4-Triazoline, 1,3-Thiazolidine, and Thiourea Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 185:7, pages 1536-1542.
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HalaM. Aly. (2009) Synthesis and Antitumor Activity of Some Novel Pyrazole and Thienopyrimidine Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 185:1, pages 211-221.
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Z.H. Ismail, M.M. Ghorab, E.M. A. Mohamed, H.M. Aly & M.S. A. El-Gaby. (2008) Antitumor Activity of Some Novel 1,2,5-Thiadiazole Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 183:10, pages 2541-2554.
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Batchu Chandrasekhar. (2008) β-Mercaptoalkanoic carboxylic esters: versatile synthons in heterocyclic chemistry . Journal of Sulfur Chemistry 29:2, pages 187-240.
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Abu-BakrA. A. M. El-Adasy. (2007) Some Nucleophilic Reactions with Isothiocyanatoazobenzene. Phosphorus, Sulfur, and Silicon and the Related Elements 182:11, pages 2625-2635.
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M. A. Metwally, E. Abdel-Latif & S. Bondock. (2007) Thiocarbamoyl derivatives as synthons in heterocyclic synthesis. Journal of Sulfur Chemistry 28:4, pages 431-466.
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RajeshwarP. Verma. (2003) Synthesis and Reactions of 1,1-Dimethyl-3-oxobutyl-isothiocyanate (DMO-ITC). Phosphorus, Sulfur, and Silicon and the Related Elements 178:2, pages 365-416.
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D. Sikora & T. Gajda. (2000) A FACILE SYNTHESIS OF DIETHYL 1- ISOTHIOCYANO)ALKYLPHOSPHONATES[1] . Phosphorus, Sulfur, and Silicon and the Related Elements 157:1, pages 201-210.
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Ayman WahbaErian. (1998) 1,1-Dicyano-2-Phenyl-3-Phenylsulphonylpropene: A Novel Reagent in Sulphone Chemistry. Synthetic Communications 28:19, pages 3549-3558.
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José Manuel García Fernandez & Carmen Ortiz Mellet. (1996) The Thiocarbonyl Group in Carbohydrate Chemistry. Sulfur reports 19:1, pages 61-159.
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BellaV. Trzhtsinskaya & NinaD. Abramova. (1991) Imidazole-2-Thiones: Synthesis, Structure, Properties. Sulfur reports 10:4, pages 389-421.
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Bubul Das, Anjali Dahiya & Bhisma K. Patel. (2024) Isothiocyanates: happy-go-lucky reagents in organic synthesis. Organic & Biomolecular Chemistry.
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Roman Nickisch, Peter Conen & Michael A. R. Meier. (2022) Polythiosemicarbazones by Condensation of Dithiosemicarbazides and Dialdehydes. Macromolecules 55:8, pages 3267-3275.
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Jih Ru Hwu, Mohit Kapoor, Nitesh K. Gupta, Shwu-Chen Tsay, Wen-Chieh Huang, Kui-Thong Tan, Yu-Chen Hu, Pieter Lyssen & Johan Neyts. (2022) Synthesis and antiviral activities of quinazolinamine–coumarin conjugates toward chikungunya and hepatitis C viruses. European Journal of Medicinal Chemistry 232, pages 114164.
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Jakub Cedrowski, Jacek Grebowski & Grzegorz Litwinienko. 2022. Lipid Oxidation in Food and Biological Systems. Lipid Oxidation in Food and Biological Systems 277 303 .
András Németh & Péter Ábrányi-Balogh. (2021) Recent Advances in the Synthesis of Isothiocyanates Using Elemental Sulfur. Catalysts 11:9, pages 1081.
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R. Nickisch, P. Conen, S. M. Gabrielsen & M. A. R. Meier. (2021) A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur. RSC Advances 11:5, pages 3134-3142.
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Diego Arauna, María Furrianca, Yolanda Espinosa-Parrilla, Eduardo Fuentes, Marcelo Alarcón & Iván Palomo. (2019) Natural Bioactive Compounds As Protectors Of Mitochondrial Dysfunction In Cardiovascular Diseases And Aging. Molecules 24:23, pages 4259.
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Amira A El-Sayed, Saad R Atta-Allah & Magdy M Hemdan. (2019) Utility of 3-(thiophen-2-yl)prop-2-enoyl isothiocyanate in heterocyclic synthesis. Journal of Chemical Research 43:9-10, pages 307-312.
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Heba Kamal Abd El-Mawgoud & Magdy Mohamed Hemdan. (2018) Utility of Lauroyl Isothiocyanate as a Scaffold in the Synthesis of Some Novel Pyrimidine Derivatives and Their Antimicrobial Assessment. Chemical and Pharmaceutical Bulletin 66:11, pages 1072-1077.
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Heba Kamal Abd El-Mawgoud, Saad Ramadan Atta-Allah & Magdy Mohamed Hemdan. (2018) Uses of 2-(Thiophene-2-carbonylcarbamothioylthio)acetic Acid as a Good Synthon for Construction of Some New Thiazole and Annulated Thiazole Derivatives. Chemical and Pharmaceutical Bulletin 66:10, pages 992-998.
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Peter J. Cossar, Cecilia C. Russell, Siobhann N. McCluskey, Dylan Pope, Paul V. Bernhardt & Adam McCluskey. (2018) Crystal Structure of Ethyl 2,4-Dimethyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate: The Product from the Reaction of Ethyl 3-Aminocrotonate, Phenylisothiocyanate and Acetic Anhydride. Journal of Chemical Crystallography 48:3, pages 91-95.
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Yuhang Zhou, Lili Lin, Xiaohua Liu, Xinyue Hu, Yan Lu, Xiying Zhang & Xiaoming Feng. (2018) Catalytic Asymmetric Diels–Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes. Angewandte Chemie International Edition 57:29, pages 9113-9116.
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Yuhang Zhou, Lili Lin, Xiaohua Liu, Xinyue Hu, Yan Lu, Xiying Zhang & Xiaoming Feng. (2018) Catalytic Asymmetric Diels–Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes. Angewandte Chemie 130:29, pages 9251-9254.
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Oleksii Yu. Voskoboynik, Svetlana V. Shishkina & Sergyi I. Kovalenko. (2018) [1,2,4]Triazino[2,3-с]quinazolines 3*. Structure and anticancer activity of products obtained from reaction of 3-(2-aminophenyl)-6-R-1,2,4-triazin-5(2H)-ones with aryl iso(thio)cyanates. Chemistry of Heterocyclic Compounds 54:7, pages 717-728.
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Mohamed S. A. El-Gaby, Mustafa M. Ghorab, Zainb H. Ismail, Soad. M. Abdel-Gawad & Hala. M. Aly. (2017) Synthesis, structural characterization and anticancer evaluation of pyrazole derivatives. Medicinal Chemistry Research 27:1, pages 72-79.
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Lucas S. Rodríguez Pirani, Carlos O. Della Védova, Mariana Geronés, Rosana M. Romano, Reinaldo Cavasso-Filho, Maofa Ge, Chunping Ma & Mauricio F. Erben. (2017) Electronic Properties and Dissociative Photoionization of Thiocyanates, Part III. The Effect of the Group’s Electronegativity in the Valence and Shallow-Core (Sulfur and Chlorine 2p) Regions of CCl 3 SCN and CCl 2 FSCN . The Journal of Physical Chemistry A 121:48, pages 9201-9210.
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Mostafa M. Ghorab, Mohamed S. A. El-Gaby, Aiten M. Soliman, Mansour S. Alsaid, Marwa M. Abdel-Aziz & Mahmoud M. Elaasser. (2017) Synthesis, docking study and biological evaluation of some new thiourea derivatives bearing benzenesulfonamide moiety. Chemistry Central Journal 11:1.
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Mostafa M. Ghorab, Mansour S. Alsaid, Mohamed S. A. El-Gaby, Mahmoud M. Elaasser & Yassin M. Nissan. (2017) Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis, biological evaluation and molecular docking. Chemistry Central Journal 11:1.
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Aisha Hossan. (2016) New route for the synthesis of N-alkyl-2-(phenylsulfonyl)anilines. Chemistry of Heterocyclic Compounds 52:8, pages 570-573.
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Harry Adams, Hannah Hodson, Michael J. Morris & Gareth A. Venting. (2016) Cyclisation of aryl acetylides with isothiocyanates: new insight into an old reaction. Tetrahedron Letters 57:12, pages 1328-1330.
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Magdy M. Hemdan & Amira A. El‐Sayed. (2015) Synthesis of Some New Heterocycles Derived from Novel 2‐(1,3‐Dioxisoindolin‐2‐yl)Benzoyl Isothiocyanate. Journal of Heterocyclic Chemistry 53:2, pages 487-492.
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Magdy Mohamed Hemdan & Amira Abd-Elhaleem El-Sayed. (2016) Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment. CHEMICAL & PHARMACEUTICAL BULLETIN Chemical and Pharmaceutical Bulletin 64:5, pages 483-489.
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Razieh Mohebat & Elahe Kafrizi. (2014) A Facile One-pot Synthesis and Heterocyclisation of ( R )-2-amino-3-((aroylcarbamothioyl)thio)propanoic Acids . Journal of Chemical Research 38:3, pages 172-174.
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Yehya M. Elkholy. (2009) Studies with phenylsulfone derivatives: Synthesis of pyrrole, thiophene and their fused derivatives. Journal of Heterocyclic Chemistry 45:4, pages 1237-1241.
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Baker Jawabrah Al-Hourani, Klaus Banert, Nermeen Gomaa & Kai Vrobel. (2008) Synthesis of functionalized thiazoles via attack of heterocyclic nucleophiles on allenyl isothiocyanates. Tetrahedron 64:23, pages 5590-5597.
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Henry Insuasty, Martín Estrada, Edward Cortés, Jairo Quiroga, Braulio Insuasty, Rodrigo Abonía, Manuel Nogueras & Justo Cobo. (2006) Regioselective synthesis of novel 4-aryl-2-ethylthio-7-methyl pyrazolo[1,5-a]-[1,3,5]-triazines. Tetrahedron Letters 47:31, pages 5441-5443.
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Boyu Zhong, Rima S. Al-Awar, Chuan Shih, John H. GrimesJr.Jr., Michal Vieth & Chafiq Hamdouchi. (2006) Novel route to the synthesis of 4-quinolyl isothiocyanates. Tetrahedron Letters 47:13, pages 2161-2164.
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S. M. Batterjee. (2005) A Novel Synthesis of Fused Heterocyclic Sulfones. Journal of the Chinese Chemical Society 52:1, pages 97-102.
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Geoffroy Sommen, Alain Comel & Gilbert Kirsch. (2003) Preparation of thieno[2,3-b]pyrroles starting from ketene-N,S-acetals. Tetrahedron 59:9, pages 1557-1564.
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Rajeshwar P. Verma. (2003) Synthesis and Reactions of 3‐Oxobutyl Isothiocyanate (OB ITC). European Journal of Organic Chemistry 2003:3, pages 415-420.
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Mohamed S. A. El‐Gaby, Jehane A. Micky, Nadia M. Taha & Marwa A. M. Sh. El‐Sharief. (2013) Antimicrobial Activity of Some Novel Thiourea, Hydrazine, Fused Pyrimidine and 2‐(4‐Substituted)anilinobenzoazole Derivatives Containing Sulfonamido Moieties. Journal of the Chinese Chemical Society 49:3, pages 407-414.
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Georges Morel & Evelyne Marchand. (2001) Diisothiocyanates as heterodienophiles or dipolarophiles in the presence of α‐thioxothioamides or mesoionic thiazoles. Heteroatom Chemistry 12:7, pages 617-624.
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Márta Palkó, Ferenc Fülöp, Ferenc Evanics & Gábor Bernáth. (2009) Synthesis and transformations of stereoisomeric ethyl 2‐isothiocyanato‐1‐cyclopentanecarboxylatesm. Journal of Heterocyclic Chemistry 37:4, pages 779-782.
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Frank Romanowski & Herbert Klenk. 2003. Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry.
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Adile Touimi Benjelloun, Georges Morel & Evelyne Marchand. (2000) 5-aminothiazolium salts as potential cyclic azomethine ylides: Base-induced cycloaddition reactions with aryl, alkyl, and benzoyl isothiocyanates. Heteroatom Chemistry 11:1, pages 16-26.
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Gerrit L'Abbé, Agna Francis, Wim Dehaen & Joris Bosman. (2010) Reactions of acyl isothiocyanates with diphenyldiazomethane. Bulletin des Sociétés Chimiques Belges 105:5, pages 253-258.
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Fresia Parrini & Raúl G.E. Morales. (1993) Electronic structure of thiocyanates Part 1. Ab initio calculations of SCN− and Li+ (SCN−). Journal of Molecular Structure: THEOCHEM 282:1-2, pages 59-63.
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Cheon-Gyu Cho & Gary H. Posner. (1992) Alkyl and aryl isothiocyanates as masked primary amines. Tetrahedron Letters 33:25, pages 3599-3602.
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