Abstract
The heterocyclic compounds which contain sulfur and nitrogen atoms have a massive effect in medicinal and pharmaceutical chemistry fields. These have been reported to have different biological activities like anti-inflammatory, antifungal, antihypertensive, and antibacterial. They also serve as multidentate ligands for various metals because of the presence of sulfur and nitrogen atoms and are therefore utilized widely in coordination chemistry to construct new scaffolds with efficient bioactivity. The LR is employed for the formation of almost all heterocyclic compounds having sulfur atom(s). The Lawesson’s reagent is a reagent which surprisingly gives unexpected reactions, consequences of which lead the chemists to novel strategies and reactions.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
(a) G. Deepika, P. Gopinath, G. Kranthi, C. Nagamani, Y.V. Jayasree, N.V. Naidu and S. Enaganti. 2012. Synthesis and antibacterial activity of some new thiazine derivatives. J. Pharm. Res. 5: 1105–1107. (b) N. Kaur. 2015. Review of microwave-assisted synthesis of benzo-fused six-membered N,N-heterocycles. Synth. Commun. 45: 300–330. (c) N. Kaur. 2017. Applications of gold catalysts for the synthesis of five-membered O-heterocycles. Inorg. Nano Met. Chem. 47: 163–187. (d) N. Kaur, Aditi and D. Kishore. 2016. A facile synthesis of face ‘D’ quinolino annulated benzazepinone analogues with its quinoline framework appended to oxadiazole, triazole and pyrazole heterocycles. J. Heterocycl. Chem. 53: 457–460.
(a) A.T. Chaviara, P.J. Cox, K.H. Repana, R.M. Papi, K.T. Papazisis, D. Zambouli, A.H. Kortsaris, D.A. Kyriakidis and C.A. Bolos. 2004. Copper(II) Schiff base coordination compounds of diene with heterocyclic aldehydes and 2-amino-5-methyl-thiazole: Synthesis, characterization, antiproliferative and antibacterial studies. Crystal structure of CudienOOCl2. J. Inorg. Biochem. 98: 1271–1283. (b) P. Sharma, N. Kaur, R. Sirohi and D. Kishore. 2013. Microwave assisted facile one pot synthesis of novel 5-carboxamido substituted analogues of 1,4-benzodiazepin-2-one of medicinal interest. Bull. Chem. Soc. Ethiop. 27: 301–307. (c) N. Kaur, Y. Verma, N. Ahlawat, P. Grewal, P. Bhardwaj and N.K. Jangid. 2020. Copper-assisted synthesis of five-membered O-heterocycles. Inorg. Nano Met. Chem. 50: 705–740. (d) S. Caron and E. Vazquez. 2003. Efficient synthesis of [6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid, a novel COX-2 inhibitor. J. Org. Chem. 68: 4104–4107.
H. Joshi, P. Upadhyay and A.J. Baxi. 1990. Studies on 4-thiazolidinones. Synthesis and antimicrobial activity of 1,4-bis(2’-aryl-5’(H)-4’-thiazolidinone-3’-ylamino)phthalazine. J. Indian Chem. Soc. 67: 779–780.
A. Al-Mulla. 2017. A review: Biological importance of heterocyclic compounds. Der Pharm. Chem. 9: 141–147.
J. Matysiak. 2006. Synthesis, antiproliferative and antifungal activities of some 2-(2,4-dihydroxyphenyl)-4H-3,1-benzothiazines. Bioorg. Med. Chem. 14: 2613–2619.
A. Macchiarulo, G. Costantino, D. Fringuelli, A. Vecchiarelli, F. Schiaffella and R. Fringuelli. 2002. 1,4-Benzothiazine and 1,4-benzoxazine imidazole derivatives with antifungal activity: A docking study. Bioorg. Med. Chem. 10: 3415–3423.
R. Fringuelli, F. Schiaffella and A. Vecchiarelli. 2001. Antifungal and immunomodulating activities of 1,4-benzothiazine azole derivatives: Review. J. Chemother. 13: 9–14.
B.S. Rathore and M. Kumar. 2006. Synthesis of 7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents. Bioorg. Med. Chem. 14: 5678–5682.
Y. Hirokawa, H. Kinoshita, T. Tanaka, T. Nakamura, K. Fujimoto, S. Kashimoto, T. Kojima and S. Kato. 2009. Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens. Bioorg. Med. Chem. Lett. 19: 170–174.
P.K. Sharma and G. Kaur. 2017. A review on antimicrobial activities of important thiazines based heterocycles. Drug Invent. Today 9: 23–25.
T. Ozturk, E. Ertas and O. Mert. 2007. Use of Lawesson’s reagent in organic syntheses. Chem. Rev. 107: 5210–5278.
M.P. Cava and M.I. Levinson. 1985. Thionation reactions of Lawesson’s reagents. Tetrahedron 41: 5061–5087.
H.Z. Lecher, R.A. Greenwood, K.C. Whitehouse and T.H. Chao. 1956. The phosphonation of aromatic compounds with phosphorus pentasulfide. J. Am. Chem. Soc. 78: 518–522.
N.C. Misra and H. Ila. 2010. 4-Bis(methylthio)methylene-2-phenyloxazol-5-one: Versatile template for synthesis of 2-phenyl-4,5-functionalized oxazoles. J. Org. Chem. 75: 5195–5202.
V. Amareshwar, N.C. Misra and H. Ila. 2011. 2-Phenyl-4-bis(methylthio)methyleneoxazol-5-one: Versatile template for diversity oriented synthesis of heterocycles. Org. Biomol. Chem. 9: 5793–5801.
S.V. Kumar, B. Saraiah, N.C. Misra and H. Ila. 2012. Synthesis of 2-phenyl-4,5-substituted oxazoles by copper-catalyzed intramolecular cyclization of functionalized enamides. J. Org. Chem. 77: 10752–10763.
S. Yugandar, A. Acharya and H. Ila. 2013. Synthesis of 2,5-bis(hetero)aryl 4’-substituted 4,5’-bisoxazoles via copper(I)-catalyzed domino reactions of activated methylene isocyanides with 2-phenyl- and 2-(2-thienyl)-4-[(aryl/heteroaryl)(methylthio)methylene]oxazol-5(4H)-ones. J. Org. Chem. 78: 3948–3960.
S.V. Kumar, G. Parameshwarappa and H. Ila. 2013. Synthesis of 2,4,5-trisubstituted thiazoles via Lawesson’s reagent-mediated chemoselective thionation-cyclization of functionalized enamides. J. Org. Chem. 78: 7362–7369.
T.D. Gordon, J. Singh, P.E. Hansen and B.A. Morgan. 1993. Synthetic approaches to the ‘azole’ peptide mimetics. Tetrahedron Lett. 34: 1901–1904.
N. Desroy, F. Moreau, S. Briet, G. LeFralliec, S. Floquet, L. Durant, V. Vongsouthi, V. Gerusz, A. Denis and S. Escaich. 2009. Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase. Bioorg. Med. Chem. 17: 1276–1289.
E. Aguliar and A.I. Meyers. 1994. Reinvestigation of a modified Hantzsch thiazole synthesis. Tetrahedron Lett. 35: 2473–2476.
M.W. Bredenkamp, C.W. Holzapfel and W.J. van Zyl. 1990. The chiral synthesis of thiazole amino acid enantiomers. Synth. Commun. 20: 2235–2249.
F.W. Foss, T.P. Mathews, Y. Kharel, P.C. Kennedy, A.H. Snyder, M.D. Davis, K.R. Lynch and T.L. MacDonald. 2009. Synthesis and biological evaluation of sphingosine kinase substrates as sphingosine-1-phosphate receptor prodrugs. Bioorg. Med. Chem. 17: 6123–6136.
F. Wolter and J. Stein. 2002. Biological activities of resveratrol and its analogs. Drugs Future 27: 949–959.
G.J. Karabatsos and N. Hsi. 1967. Structural studies by nuclear magnetic resonance - XI. Tetrahedron 23: 1079–1095.
S. Bertini, V. Calderone, I. Carboni, R. Maffei, A. Martelli, A. Martinelli, F. Minutolo, M. Rajabi, L. Testai, T. Tuccinardi, R. Ghidoni and M. Macchia. 2010. Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties. Bioorg. Med. Chem. 18: 6715–6724.
J. Mehrzad, M. Rajabi and M.A. Khalilzadeh. 2010. Design and antiproliferative activity of 2-(3,5-dihydroxyphenyl)-6-hydroxybenzothiazole (DHB) on PC-3 prostate cancer cell line. Iran. J. Org. Chem. 2: 487–489.
R.A. Irgashev, A.A. Karmatsky, P.A. Slepukhin, G.L. Rusinov and V.N. Charushin. 2013. A convenient approach to the design and synthesis of indolo[3,2-c]coumarins via the microwave-assisted Cadogan reaction. Tetrahedron Lett. 54: 5734–5738.
T.M. Potewar, K.T. Petrova and M.T. Barros. 2013. Efficient microwave assisted synthesis of novel 1,2,3-triazole-sucrose derivatives by cycloaddition reaction of sucrose azides and terminal alkynes. Carbohydr. Res. 379: 60–67.
R.C. Lian, M.H. Lin, M.H. Liao, J.J. Fu, Y.C. Wu, F.R. Chang, C.C. Wu, M.J. Wu and P.S. Pan. 2014. Direct synthesis of the arylboronic acid analogues of phenylglycine via microwave-assisted four-component Ugi reaction. Tetrahedron 70: 1800–1804.
M.Y. Mentese, H. Bayrak, Y. Uygun, A. Mermer, S. Ulker, S.A. Karaoglu and N. Demirbas. 2013. Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities. Eur. J. Med. Chem. 67: 230–242.
F. Messina and O. Rosati. 2013. Superheated water as solvent in microwave assisted organic synthesis of compounds of valuable pharmaceutical interest. Curr. Org. Chem. 17: 1158–1178.
P. Appukkuttan, V.P. Mehta and E.V. van der Eycken. 2010. Microwave-assisted cycloaddition reactions. Chem. Soc. Rev. 39: 1467–1477.
X. Zhang, H. Jiang, D. Ye, H. Sun and H. Liu. 2009. Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water. Green Chem. 11: 1881–1888.
B. Maiti, K. Chanda, M. Selvaraju, C.C. Tseng and C.M. Sun. 2013. Multicomponent solvent-free synthesis of benzimidazolyl imidazo[1,2-a]pyridine under microwave irradiation. ACS Comb. Sci. 15: 291–297.
A. Walia, S. Kang and R.B. Silverman. 2013. Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection. J. Org. Chem. 78: 10931–10937.
E.F. Dimauro and J.M. Kennedy. 2007. Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot. J. Org. Chem. 72: 1013–1016.
R.B. Sparks and A.P. Combs. 2004. Microwave-assisted synthesis of 2,4,5-triaryl-imidazole; a novel thermally induced N-hydroxyimidazole N-O bond cleavage. Org. Lett. 6: 2473–2475.
H.D. Patel, S.M. Divatia and E. de Clercq. 2013. Synthesis of some novel thiosemicarbazone derivatives having anti-cancer, anti-HIV as well as anti-bacterial activity. Indian J. Chem. Sect. B 52: 535–545.
S.M. Prajapati, R.H. Vekariya, K.D. Patel, S.N. Panchal, H.D. Patel, D.P. Rajani and S. Rajani. 2014. Synthesis and in vitro antibacterial and antifungal evaluation of quinoline analogue azetidine and thiazolidine derivatives. Int. Lett. Chem. Phys. Astron. 20: 195–210.
N.P. Prajapati, R.H. Vekariya and H.D. Patel. 2015. Microwave induced facile one-pot access to diverse 2-cyanobenzothiazole - a key intermediate for the synthesis of firefly luciferin. Int. Lett. Chem. Phys. Astron. 44: 81–89.
J.A. Seijas, M.P. Vázquez-Tato, M.R. Carballido-Reboredo, J. Crecente-Campo and L. Romar-López. 2007. Lawesson’s reagent and microwaves: A new efficient access to benzoxazoles and benzothiazoles from carboxylic acids under solvent-free conditions. Synlett 2: 313–317.
C.L. Penney, P. Shah and S. Landi. 1985. A simple method for the synthesis of long-chain alkyl esters of amino acids. J. Org. Chem. 50: 1457–1459.
A.A. Kiryanov, P. Sampson and A.J. Seed. 2001. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson’s reagent-mediated cyclization under microwave irradiation: Applications for liquid crystal synthesis. J. Org. Chem. 66: 7925–7929.
M. Yokoyama, Y. Menjo, M. Watanabe and H. Togo. 1994. Synthesis of oxazoles and thiazoles using thioimidates. Synthesis 12: 1467–1470.
T.P. Andersen, A.-B.A.G. Ghattas and S.-O. Lawesson. 1983. Studies on amino acids and peptides - IV. Tetrahedron 39: 3419–3427.
Z. Kaleta, G. Tarkanyi, A. Gomory, F. Kalman, T. Nagy and T. Soos. 2006. Synthesis and application of a fluorous Lawesson’s reagent: Convenient chromatography-free product purification. Org. Lett. 8: 1093–1095.
Z. Kaleta, B.T. Makowski, T. Soos and R. Dembinski. 2006. Thionation using fluorous Lawesson’s reagent. Org. Lett. 8: 1625–1628.
L. Friedman and H. Shechter. 1961. Dimethylformamide as a useful solvent in preparing nitriles from aryl halides and cuprous cyanide; improved isolation techniques. J. Org. Chem. 26: 2522–2524.
M.M. Murza, T.R. Prosochina, M.G. Safarov and E.A. Kantor. 2001. Synthesis and quantum-chemical study of liquid-crystal derivatives of thiazole. Chem. Heterocycl. Compd. (Engl. Transl.) 37: 1258–1265.
Z.K. Kuvatov, M.G. Safarov and M.M. Murza. 2004. New derivatives of thiazole with mesomorphous properties. Chem. Heterocycl. Compd. (Engl. Transl.) 40: 500–502.
A.S. Golovanov, M.M. Murza and M.G. Safarov. 1997. Novel mesomorphic Schiff bases. Chem. Heterocycl. Compd. 33: 1350–1351.
M.M. Murza, A.S. Golovanov and M.G. Safarov. 1996. New liquid crystal derivatives of thiazole. Chem. Heterocycl. Compd. (Engl. Transl.) 32: 477–478.
A.M. Grubb, S. Hasan, A.A. Kiryanov, P. Sampson and A.J. Seed. 2009. The synthesis and physical evaluation of 5-alkoxy-1,3-thiazoles prepared via Lawesson’s reagent-mediated cyclisation of α-benzamido esters. Liq. Cryst. 36: 443–453.
M. Jesberger, T.P. Davies and L. Barner. 2003. Applications of Lawesson’s reagent in organic and organometallic syntheses. Synthesis 13: 1929–1958.
D.L.J. Clive, S. Hisaindee and D.M. Coltart. 2003. Derivatized amino acids relevant to native peptide synthesis by chemical ligation and acyl transfer. J. Org. Chem. 68: 9247–9254.
T. Patonay, E. Juhasz-Toth and A. Benyei. 2002. Base-induced coupling of α-azido ketones with aldehydes - an easy and efficient route to trifunctionalized synthons 2-azido-3-hydroxyketones, 2-acylaziridines, and 2-acylspiroaziridines. Eur. J. Org. Chem. 2: 285–295.
N.J. Gilmore, S. Jones and M.P. Muldowney. 2004. Synthetic applicability and in situ recycling of a B-methoxy oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. Org. Lett. 6: 2805–2808.
S. Takami and M. Irie. 2004. Synthesis and photochromic properties of novel yellow developing photochromic compounds. Tetrahedron 60: 6155–6161.
H.Z. Lecher, R.A. Greenwood, K.C. Whitehouse and T.H. Cho. 1956. The phosphonation of aromatic compounds with phosphorus pentasulfide. J. Am. Chem. Soc. 78: 5018–5022.
J. Lee, S.-H. Lee, H.J. Seo, E.-J. Son, S.H. Lee, M.E. Jung, M. Lee, H.-K. Han, J. Kim, J. Kang and J. Lee. 2010. Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners. Bioorg. Med. Chem. 18: 2178–2194.
M.J. Kim, J. Lee, S.Y. Kang, S.-H. Lee, E.-J. Son, M.E. Jung, S.H. Lee, K.-S. Song, M. Lee, H.-K. Han, J. Kim and J. Lee. 2010. Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: Pyridazinylmethylphenyl glucoside congeners. Bioorg. Med. Chem. Lett. 20: 3420–3425.
K.-S. Song, S.H. Lee, M.J. Kim, H.J. Seo, J. Lee, S.-H. Lee, M.E. Jung, E.-J. Son, M.W. Lee, J. Kim and J. Lee. 2011. Synthesis and SAR of thiazolylmethylphenyl glucoside as novel C-aryl glucoside SGLT2 inhibitors. ACS Med. Chem. Lett. 2: 182–187.
T. Besson and V. Thiery. 2006. Microwave-assisted synthesis of sulfur and nitrogen-containing heterocycles. Top. Heterocycl. Chem. 1: 59–78.
O. Uchikawa, K. Fukatsu and T. Aono. 1994. Aminothiazole derivatives. I. A convenient synthesis of monocyclic and condensed 5-aminothiazole derivatives. J. Heterocycl. Chem. 31: 877–887.
T. Vojkovsky. 1995. Detection of secondary amines on solid phase. Pept. Res. 8: 236–237.
J.F. Sanz-Cervera, R. Blasco, J. Piera, M. Cynamon, I. Ibanez, M. Murguia and S. Fustero. 2009. Solution versus fluorous versus solid-phase synthesis of 2,5-disubstituted 1,3-azoles. Preliminary antibacterial activity studies. J. Org. Chem. 74: 8988–8996.
P. Wipf, C. Jenny and H. Heimgartner. 1987. 2,4-Bis(4-methylpheylthio)-1,3,2λ5,4λ5-dithiadiphosphetan-2,4-dithion: Ein neues reagens zur Schwefelung von N,N-disubstituierten amiden. Helv. Chim. Acta 70: 1001–1011.
D. Obrecht and H. Heimgartner. 1982. A convenient synthesis of 2-oxazolin-5-ones and related compounds via amide cyclization. Chimia 36: 78–81.
D. Obrecht, R. Prewo, J.H. Bieri and H. Heimgartner. 1982. 1,3-Dipolare cycloadditionen von 2-(benzonitrilio)-2-propanid mit 4,4-dimethyl-2-phenyl-2-thiazolin-5-thion und schwefelkohlenstoff. Helv. Chim. Acta 65: 1825–1836.
C. Jenny and H. Heimgartner. 1986. Synthese von 4,4-disubstituierten 1,3-thiazol-5(4H)-thionen. Helv. Chim. Acta 69: 374–388.
M.J. Thompson and B. Chen. 2008. Versatile assembly of 5-aminothiazoles based on the Ugi four-component coupling. Tetrahedron Lett. 49: 5324–5327.
M.J. Thompson and B. Chen. 2009. Ugi reactions with ammonia offer rapid access to a wide range of 5-aminothiazole and oxazole derivatives. J. Org. Chem. 74: 7084–7092.
G. Koopmanschap, E. Ruijter and V.A.O. Romano. 2014. Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics. Beilstein J. Org. Chem. 10: 544–598.
M.C. Bagley, K.E. Bashford, C.L. Hesketh and C.J. Moody. 2000. Total synthesis of the thiopeptide promothiocin A. J. Am. Chem. Soc. 122: 3301–3313.
J.R. Davies, P.D. Kane and C.J. Moody. 2005. The diazo route to diazonamide A. Studies on the indole bis-oxazole fragment. J. Org. Chem. 70: 7305–7316.
A. Ford, H. Miel, A. Ring, C.N. Slattery, A.R. Maguire and M.A. McKervey. 2015. Modern organic synthesis with α-diazocarbonyl compounds. Chem. Rev. 115: 9981–10080.
B.S. Drach, I.Y. Dolgushina and A.V. Kirsanov. 1973. Reaction of omega-chlorine-omega-acylamino-acetophenones with thioacetamide. Zh. Org. Khim. 9: 414–419.
B.S. Drach, I.Y. Dolgushina and A.D. Sinitsa. 1974. Some cyclization reactions of ω-chloro-ω-acylamidoacetophenones. Khim. Geterotsikl. Soedin. 7: 928–931.
B.S. Drach, I.Y. Dolgushina and A.D. Sinitsa. 1975. Verwendung von omega-chlor-omega-acylaminoacetophenon zur synthese phosphorylierter oxazole. Zh. Obshch. Khim. 45: 1251–1255.
R.A. Cherkasov, G.A. Kutyrev and A.N. Pudovik. 1985. Tetrahedron report number 186. Organothiophosphorus reagents in organic synthesis. Tetrahedron 41: 2567–2624.
S.I. Zav’yalov, T.K. Budkova and M.N. Larionova. 1976. New method for conversion of N-acyl-α-aminoketones to substituted thiazoles. Bull. Acad. Sci. USSR Div. Chem. Sci. 25: 1353–1356.
T. Nishio and M. Ori. 2001. Thionation of ω-acylamino ketones with Lawesson’s reagent: Convenient synthesis of 1,3-thiazoles and 4H-1,3-thiazines. Helv. Chim. Acta 84: 2347–2354.
A.G. Belyuga, V.S. Brovarets and B.S. Drach. 2004. Phosphorus pentasulfide and Lawesson reagent in synthesis of 1,3-thiazole-4-thiol derivatives. Russ. J. Gen. Chem. 74: 1418–1422.
R.A. Hughes, S.P. Thompson, L. Alcaraz and C.J. Moody. 2004. Total synthesis of the thiopeptide amythiamicin D. Chem. Commun. 8: 946–948.
C. Jenny and H. Heimgartner. 1989. Bildung von 5,6-dihydro-1,3(4H)-thiazin-4-carbonsäure-estern aus 4-allyl-1,3-thiazol-5(4H)-onen. Helv. Chim. Acta 72: 1639–1646.
C. Bengtsson. 2013. Synthesis of substituted ring-fused 2-pyridones and applications in chemical biology. PhD Thesis, Umea University.
R.A. Hughes, S.P. Thompson, L. Alcaraz and C.J. Moody. 2005. Total synthesis of the thiopeptide antibiotic amythiamicin D. J. Am. Chem. Soc. 127: 15644–15651.
J.R. Davies, P.D. Kane and C.J. Moody. 2004. N-H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles. Tetrahedron 60: 3967–3977.
I. Thomsen, K. Clausen, S. Scheibye and S.O. Lawesson. 1984. Thiation with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide: N-Methylthiopyrrolidone. Org. Synth. 62: 158–164.
J.P. Freeman. 1990. John Wiley & Sons: New York, NY, 372.
M.H. Zheng, J.Y. Jin, W. Sun and C.H. Yan. 2006. A new series of fluorescent 5-methoxy-2-pyridylthiazoles with a pH-sensitive dual-emission. New J. Chem. 30: 1192–1196.
L.G. Lee, C.H. Chen and L.A. Chiu. 1986. Thiazole orange: A new dye for reiculocyte analysis. Cytometry 7: 508–517.
Z.X. Li, L.Y. Liao, W. Sun, C.H. Xu, C. Zhang, C.J. Fang and C.H. Yan. 2008. Re-configurable cascade circuit in a photo- and chemical-switchable fluorescent diarylethene derivative. J. Phys. Chem. C 112: 5190–5196.
X.C. Hu, S. Wei, Z. Chao, B.Y. Chun, F.C. Jie, L.W. Tao, H.Y. Yi and Y.C. Hua. 2009. Chemical approaches for mimicking logic functions within fluorescent MPT dyes. Sci. Chin. Ser. B: Chem. 52: 700–714.
M.S.J. Foreman and J.D. Woollins. 2000. Organo-P-S and P-Se heterocycles. J. Chem. Soc. Dalton Trans. 10: 1533–1543.
R. Markovic, A. Rasovic, M. Baranac, M. Stojanovic, P.J. Steel and S. Jovetic. 2004. Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. J. Serb. Chem. Soc. 69: 909–918.
R. Markovic, M. Baranac and S. Jovetic. 2003. A novel and efficient 4-oxothiazolidine-1,2-dithiole rearrangement induced by Lawesson’s reagent. Tetrahedron Lett. 44: 7087–7090.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2022 The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Kaur, N. (2022). Thiazole Synthesis. In: Lawesson’s Reagent in Heterocycle Synthesis. Springer, Singapore. https://doi.org/10.1007/978-981-16-4655-3_2
Download citation
DOI: https://doi.org/10.1007/978-981-16-4655-3_2
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-16-4654-6
Online ISBN: 978-981-16-4655-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)