Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2024; 35(18): 2063-2083
DOI: 10.1055/s-0042-1751549
DOI: 10.1055/s-0042-1751549
account
Adventures in the Chemistry of Nitro Compounds
Abstract
The present article provides an overview of our work related to cyclization reactions of nitro-substituted electrophilic building blocks with various nucleophiles. As electrophiles, we used nitro-substituted benzoylacetones, 3-ethoxy-2-nitro-2-en-1-ones, 2-nitrobenzoyl chlorides, 4-chloro-3-nitrocoumarin, 2-nitromalonic aldehyde, 3-nitrochromone and 1-(2-chloro-5-nitrophenyl)prop-2-yn-1-ones. As nucleophiles, 1,3-dicarbonyl compounds, 1,3-bis(silyloxy)-1,3-butadienes, (heterocyclic) enamines, hydroxylamine, hydrazines, amines and amino esters were employed. The products include a variety of nitro-substituted carbo- and heterocycles that are not readily available by other methods. The electron-withdrawing nitro group can be easily transformed into an electron-donating amino group which is not only pharmacologically relevant, but can also act as a nucleophile in inter- and intramolecular reactions with electrophiles, such as aldehydes, and can be converted into other functional groups. The nitro group has the capacity to activate compounds for regioselective palladium-catalyzed CH-arylation reactions. Inter- and intramolecular CH arylations of nitro-substituted heterocyclic building blocks, such as 4-nitropyrazoles, 4-nitroimidazoles, 2-nitroindole and nitro-substituted purine analogues, allow for a convenient diversity-oriented approach to the corresponding arylated products. In addition, the nitro group can act as a leaving group in SNAr reactions. Various fused benzofuro[3,2-b]pyridines were prepared by intramolecular SNAr reactions of 2-(hydroxyphenyl)-3-nitropyridines.
1 Introduction
2 Cyclizations of 1,3-Bis(silyloxy)-1,3-butadienes
3 Cyclizations of Heterocyclic Enamines
4 Reactions of Simple Nitro-Substituted Heterocycles
5 Hydroamination Reactions of Alkynes
6 Miscellaneous
7 Conclusions
Publication History
Received: 22 November 2023
Accepted after revision: 13 December 2023
Article published online:
30 January 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Feuer H. Nitro and Nitroso Groups, Part 2, Vol. 2. In Patai’s Chemistry of Functional Groups . John Wiley & Sons Ltd; Weinheim: 1970. ISBN 978-0-470-77117-4
- 1b Patai S. Nitro and Nitroso Groups, Sup. F, Part 2, Vol. 2. In Patai’s Chemistry of Functional Groups . John Wiley & Sons Ltd; Weinheim: 1982. ISBN 978-0-470-77167-9
- 1c Patai S. Amino, Nitroso and Nitro Compounds and Their Derivatives, Sup. F, Part 1, Vol. 1. In Patai's Chemistry of Functional Groups. John Wiley & Sons Ltd; Weinheim: 1982. ISBN 978-0-470-77166-2
- 1d Booth G. Nitro Compounds, Aromatic. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim: 2000
- 2 Review: Nepali K, Lee HY, Liou JP. J. Med. Chem. 2019; 62: 2851
- 3a Díaz-Salazar H, Rodríguez-Colín JC, Vazquez-Chavez J, Hernández-Rodríguez M. J. Org. Chem. 2023; 88: 8150
- 3b Trost BM, Chadiri MR. J. Am. Chem. Soc. 1984; 106: 7260 This means that originally the term was used for compounds that can react both as a nucleophile and electrophile and not for functional groups, which need a chemical transformation to change their properties.
- 4a For cyclizations of dianions and other dinucleophiles with oxalic acid-bis(imidoyl)dichlorides: Langer P, Döring M. Eur. J. Org. Chem. 2002; 221
- 4b For 1,3-bis(trimethylsilyloxy)-1,3-butadienes in general, see: Langer P. Synthesis 2002; 441
- 4c For cyclizations of free dianions with dielectrophiles in general: Langer P, Freiberg W. Chem. Rev. 2004; 104: 4125
- 4d For cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride: Langer P. Synlett 2006; 3369
- 4e For the synthesis of 2-(alkylidene)tetrahydrofurans: Bellur E, Feist H, Langer P. Tetrahedron 2007; 63: 10865
- 4f For formal [3+3] cyclizations: Feist H, Langer P. Synthesis 2007; 327
- 4g For cyclizations with iminium salts: Langer P. Synlett 2007; 1016
- 4h For cyclizations with chromones: Langer P. Eur. J. Org. Chem. 2007; 2233
- 4i For (2,4-dioxobutylidene)phosphoranes: Feist H, Langer P. Synthesis 2008; 3877
- 4j For fluorine-containing products: Langer P. Synlett 2009; 2205
- 4k For sulfur-containing products: Nawaz P, Sher M, Langer P. Synlett 2010; 2383
- 4l For cyclizations of oxime and hydrazine dianions: Dang TT, Dang TT, Langer P. Synlett 2011; 2633
- 4m For cyclizations with 3-alkoxy-2-en-1-ones: Karapetyan G, Dang TT, Sher M, Ghochikyan TV, Saghyan AS, Langer P. Curr. Org. Chem. 2012; 16: 557
- 4n For cyclizations of 1,1-bis(trimethylsilyloxy)ketene acetals: Dang TT, Kelzhanova NK, Abilov ZA, Turmukhanova MZ, Langer P. Synlett 2012; 23: 1283
- 4o For chlorine-containing products: Hassan Z, Langer P. Synlett 2019; 30: 665
- 4p For cyclizations with acid chlorides: Langer P. Synlett 2021; 32: 2036
- 4q For reactions of the dianion of 1,1-diphenylacetone: Langer P. Synlett 2023; 34: 414
- 4r For applications in the field of cyclopropanes: Langer P. Synlett 2023; 34: 1765
- 4s For applications in the field of epihalohydrins: Langer P. Synlett 2023; 34: 1953
- 5a Riahi A, Shkoor M, Khera RA, Reinke H, Langer P. Tetrahedron Lett. 2009; 50: 3017
- 5b Riahi A, Shkoor M, Fatunsin O, Yawer MA, Hussain I, Fischer C, Langer P. Tetrahedron 2009; 65: 9300
- 6a Werbel LM, Cook PD, Elslager EF, Hung JH, Johnson JL, Kesten SJ, McNamara DJ, Ortwine DF, Worth DF. J. Med. Chem. 1986; 29: 924
- 6b Take K, Okumura K, Takimoto K, Kato M, Ohtsuka M, Shiokawa Y. Chem. Pharm. Bull. 1991; 39: 2915
- 6c Astles PC, Brown TJ, Cox P, Halley F, Lockey PM, Mccarthy C, Mclay IM, Majid TN, Morley AD. Bioorg. Med. Chem. Lett. 1997; 7: 907
- 6d Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Takahashi M, Kotera J, Ikeo T. J. Med. Chem. 1999; 42: 1293
- 6e Sun L, Tran N, Liang C, Tang F, Rice A, Schreck R, Waltz K, Shawver LK, McMahon G, Tang C. J. Med. Chem. 1999; 42: 5120
- 6f Poupart M.-A, Cameron DR, Chabot C, Ghiro E, Goudreau N, Goulet S, Poirier M, Tsantrizos YS. J. Org. Chem. 2001; 66: 4743
- 6g Parikh V, Welch WM, Schmidt AW. Bioorg. Med. Chem. Lett. 2003; 13: 269
- 6h Wang L, Wang GT, Wang X, Tong Y, Sullivan G, Park D, Leonard NM, Li Q, Cohen J, Gu W.-Z, Zhang H, Bauch JL, Jakob CG, Hutchins CW, Stoll VS, Marsh K, Rosenberg SH, Sham HL, Lin N.-H. J. Med. Chem. 2004; 47: 612
- 6i Sheppard GS, Kawai M, Craig RA, Davidson DJ, Majest SM, Bell RL, Henkin J. Bioorg. Med. Chem. Lett. 2004; 14: 965
- 6j Mor M, Rivara S, Lodola A, Plazzi PV, Tarzia G, Duranti A, Tontini A, Piersanti G, Kathuria S, Piomelli D. J. Med. Chem. 2004; 47: 4998
- 6k Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Naruto S, Sugano Y. Bioorg. Med. Chem. Lett. 2004; 14: 4383
- 7a Castedo L, Lopez S, de Lera AR, Villaverde C. Phytochemistry 1989; 28: 251
- 7b Satou T, Akao N, Matsuhashi R, Koike K, Fujita K, Nikaido T. Biol. Pharm. Bull. 2002; 25: 1651
- 7c Chen J.-J, Chang Y.-L, Teng C.-M, Lin W.-Y, Chen Y.-C, Chen I.-S. Planta Med. 2001; 67: 423
- 7d Ng KM, Gray AI, Waterman PG. Phytochemistry 1987; 26: 3251
- 7e Tsai I.-L, Wun M.-F, Teng C.-M, Ishikawa T, Chen I.-S. Phytochemistry 1998; 48: 1377
- 7f Chen J.-J, Fang H.-Y, Duh C.-Y, Chen I.-S. Planta Med. 2005; 71: 470
- 8a Tsai I.-L, Fang S.-C, Ishikawa T, Chang C.-T, Chen I.-S. Phytochemistry 1997; 44: 1383
- 8b Tsai I.-L, Wun M.-F, Teng C.-M, Ishikawa T, Chen I.-S. Phytochemistry 1998; 48: 1377
- 8c Chou H.-C, Chen J.-J, Duh C.-Y, Huang T.-F, Chen I.-S. Planta Med. 2005; 71: 1078
- 8d Vardamides JC, Dongmo AB, Meyer M, Ndom JC, Azebaze AG. B, Zounda MR. S, Sielinou VT, Ndemangou B, Nkengfack AE, Ngando TM, Fomum ZT. Chem. Pharm. Bull. 2006; 54: 1034
- 8e Llabres JM, Viladomat F, Bastida J, Codina C, Rubiralta M. Phytochemistry 1986; 25: 2637
- 8f Torres JC, Pinto AC, Garden SJ. Tetrahedron 2004; 60: 9889
- 8g Ganton MD, Kerr MA. Org. Lett. 2005; 7: 4777
- 9a Brown H, Kipp H. Cancer Res. 1970; 30: 2089
- 9b Liang E, Proudfoot J, Yazdanian M. Pharm. Res. 2000; 17: 1168
- 9c Lee EH, Kim H.-M. Pharmacology 1998; 56: 223
- 9d Liptay S, Fulda S, Schanbacher M, Bourteele S, Ferri KF, Kroemer G, Adler G, Debatin KM, Schmid RM. Br. J. Pharmacol. 2002; 137: 608
- 9e Korpimaki T, Hagren V, Brockmann E.-C, Tuomola M. Anal. Chem. 2004; 76: 3091
- 9f Matsson P, Bergstroem CA. S, Nagahara N, Tavelin S, Norinder U, Artursson P. J. Med. Chem. 2005; 48: 604
- 9g Irvine JD, Takahashi L, Lockhart K, Cheong J, Tolan JW. J. Pharm. Sci. 1999; 88: 28
- 9h Kimura I, Kawasaki M, Nagahama S, Matsuda A, Kataoka M, Kokuba Y. Arzneim. Forsch. 1998; 48: 1091
- 9i Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS. Biochem. Pharmacol. 1997; 53: 1901
- 9j Hibi S, Okamoto Y, Tagami K, Numata H, Kobayashi N. J. Med. Chem. 1994; 37: 3062
- 9k Pellicciari R, Garzon-Aburbeh A, Natalini B, Marinozzi M, Clerici C. J. Med. Chem. 1993; 36: 4201
- 9l Brown JP, McGarraugh GV, Parkinson TM, Wingard RE, Onderdonk AB. J. Med. Chem. 1983; 26: 1300
- 10a Industrial Dyes . Hunger K. Wiley; New York: 2002
- 10b Brown H, Kipp H. Cancer Res. 1970; 30: 2089
- 10c Liang E, Proudfoot J, Yazdanian M. Pharm. Res. 2000; 17: 1168
- 10d Lee EH, Kim H.-M. Pharmacology 1998; 56: 223
- 10e Liptay S, Fulda S, Schanbacher M, Bourteele S, Ferri KF, Kroemer G, Adler G, Debatin KM, Schmid RM. Br. J. Pharmacol. 2002; 137: 608
- 10f Korpimaki T, Hagren V, Brockmann E.-C, Tuomola M. Anal. Chem. 2004; 76: 3091
- 10g Matsson P, Bergstroem CA. S, Nagahara N, Tavelin S, Norinder U, Artursson P. J. Med. Chem. 2005; 48: 604
- 10h Irvine JD, Takahashi L, Lockhart K, Cheong J, Tolan JW. J. Pharm. Sci. 1999; 88: 28
- 10i Kimura I, Kawasaki M, Nagahama S, Matsuda A, Kataoka M, Kokuba Y. Arzneim. Forsch. 1998; 48: 1091
- 10j Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS. Biochem. Pharmacol. 1997; 53: 1901
- 10k Hibi S, Okamoto Y, Tagami K, Numata H, Kobayashi N. J. Med. Chem. 1994; 37: 3062
- 10l Pellicciari R, Garzon-Aburbeh A, Natalini B, Marinozzi M, Clerici C. J. Med. Chem. 1993; 36: 4201
- 10m Brown JP, McGarraugh GV, Parkinson TM, Wingard RE, Onderdonk AB. J. Med. Chem. 1983; 26: 1300
- 10n Baures PW, Peterson SA, Kelly JW. Bioorg. Med. Chem. 1998; 6: 1389
- 11a Hefner J, Langer P. Tetrahedron Lett. 2008; 49: 2262
- 11b Hefner J, Ladzik S, Lalk M, Kelzhanova N, Saginayev AT, Rahman Q, Villinger A, Fischer C, Langer P. Z. Naturforsch., B: J. Chem. Sci. 2014; 69: 924
- 11c Imran M, Iqbal I, Abilov ZA, Langer P. Phosphorus, Sulfur Silicon Relat. Elem. 2014; 189: 255
- 12 Rahn T, Appel B, Baumann W, Jiao H, Fischer C, Börner A, Langer P. Org. Biomol. Chem. 2009; 7: 1931
- 13a Eleya N, Mahal A, Villinger A, Langer P. Adv. Synth. Catal. 2011; 353: 2761 ; and references cited therein
- 13b Kuhrt D, Ejaz SA, Afzal S, Khan SU, Lecka J, Sévigny J, Ehlers P, Spannenberg A, Iqbal J, Langer P. Eur. J. Med. Chem. 2017; 816
- 14 Zeeshan M, Iaroshenko VO, Dudkin S, Volochnyuk D, Langer P. Tetrahedron Lett. 2010; 51: 3897
- 15a Kennedy RO, Thorenes RD. Coumarins: Biology, Applications, Mode of Action . Wiley; Chichester: 1997
- 15b Yu DL, Suzuki M, Xie L, Morris-Natschke SL, Lee KH. Med. Res. Rev. 2003; 23: 322
- 15c Fylaktakidou KC, Hadjipavlou-Litina DJ, Litines KE, Nicolaides DN. Curr. Pharm. Des. 2004; 10: 3813
- 15d Borges F, Roleira F, Milhazes N, Santana L, Uriarte E. Curr. Med. Chem. 2005; 12: 887
- 15e Chen L, Xu MH. Adv. Synth. Catal. 2009; 351: 2005
- 16 Fatunsin O, Iaroshenko VO, Dudkin S, Shkoor M, Volochnyuk D, Gevorgyan A, Langer P. Synlett 2010; 1533
- 17a Zielke CI, Suelter CH. Purine, Purine Nucleoside, and Purine Nucleotide Aminohydrolases . In The Enzymes . Boyer PD. Academic Press; New York: 1971: 47
- 17b Niedzwicki JG, Kouttab NM, Mayer KH, Carpenter CC, Parks RE. Jr, Abushanab E, Abernethy DR. J. Acquired Immune Defic. Syndr. 1991; 4: 178
- 17c Salvatore D, Claudio MM, Anna PM. Clin. Chem. 1987; 33: 1675
- 17d Valenzuela A, Blanco J, Callebaut C, Jacotot E, Lluis C, Hovanessian AG, Franco R. J. Immunol. 1997; 158: 3721
- 17e Ungerer JP. J, Oosthuizen HM, Retief JH, Bissbort SH. Chest 1994; 106: 33
- 17f Banales JL, Rivera-Martinez E, Perez-Gonzalez L, Selman M, Raymond Y, Nava A. Arch. Med. Res. 1999; 30: 358
- 17g Chiba S, Matsumoto H, Saitoh M, Kasahara M, Matsuya M, Kashiwagi MA. J. Neurol. Sci. 1995; 132: 170
- 17h Gakis C. Eur. Respir. J. 1996; 9: 632
- 17i Demeocq F, Viallard JL, Boumsell L, Richard Y, Chassgne J, Plagne R, Lemerle J, Bernard A. Leuk. Res. 1982; 6: 211
- 17j Carlucci F, Rosi F, Di Pietro C, Marinello E. Biochim. Biophys. Acta 1997; 1360: 203
- 17k Silverman RB. The Organic Chemistry of Drug Design, and Drug Action, 2nd Ed. 2004; 617 ISBN 0-12-643732-7
- 17l Shewach DS, Krawczyk SH, Acevedo OL, Townsend LB. Biochem. Pharmacol. 1992; 44: 1697
- 17m Frieden C, Kurz LC, Gilbert HR. Biochemistry 1980; 19: 5303
- 19a Novartis AG. WO 2007/84786 A1, 2007 ; Chem. Abstr. 2007, 147, 189196
- 19b Takeuchi I, Hamada Y, Hirota M. Chem. Pharm. Bull. 1993; 41: 747
- 20 Iaroshenko VO, Vilches-Herrera M, Gevorgyan A, Mkrtchyan S, Arakelyan K, Ostrovskyi D, Abbasi MS. A, Supe L, Hakobyan A, Villinger A, Volochnyuk DM, Tolmachev A, Langer P. Tetrahedron 2013; 69: 1217
- 21 Iaroshenko VO, Gevorgyan A, Mkrtchyan S, Grigoryan T, Movsisyan E, Villinger A, Langer P. ChemCatChem 2015; 7: 316
- 22a Becket GJ. P, Ellis GP. Tetrahedron Lett. 1976; 9: 719
- 22b Connor DT, Young PA, von Strandtmann M. J. Heterocycl. Chem. 1981; 18: 697
- 22c Haas G, Stanton JL, Winkler T. J. Heterocycl. Chem. 1981; 18: 619
- 22d Takagi K, Tanaka M, Murakami Y, Ogura K, Ishii K, Morita H, Aotsuka T. J. Heterocycl. Chem. 1987; 24: 1003
- 22e Perrella FW, Chen S.-F, Behrens DL, Kaltenbach RF. III, Seitz SP. J. Med. Chem. 1994; 37: 2232
- 23 Ostrovskyi D, Iaroshenko VO, Petrosyan A, Dudkin S, Ali I, Villinger A, Tolmachev A, Langer P. Synlett 2010; 2299
- 24 Iaroshenko VO, Mkrtchyan S, Gevorgyan A, Vilches-Herrera M, Sevenard DV, Villinger A, Ghochikyan TV, Saghyan AS, Sosnovskikh VY, Langer P. Tetrahedron 2012; 68: 2532
- 25a Dubois L, Evanno Y, Gille C, Malanda A. WO 2009112677, 2009
- 25b Boyd E, Brookfield F, Gridley J, Honold K, Lau R, Scheiblich S. WO 2007014707, 2007
- 25c Engh R, Hertenberger H, Honold K, Masjost B, Rueger P, Schaefer W, Scheiblich S, Schwaiger M. WO 2007017143, 2007
- 25d Honold K, Kaluza K, Masjost B, Schaefer W, Scheiblich S. WO 2006066914, 2006
- 26a Kanishchev MI, Korneeva N, Shevelev SA, Fainzilberg AA. Chem. Heterocycl. Compd. 1988; 24: 353 ; and references cited therein
- 26b Lusardi M, Spallarossa A, Brullo C. Int. J. Mol. Sci. 2023; 25: 7834
- 27 Iaroshenko VO, Gevorgyan A, Davydova O, Langer P. J. Org. Chem. 2014; 79: 2906
- 28 Review: Ang CW, Jarrad AM, Cooper MA, Blaskovich MA. T. J. Med. Chem. 2017; 60: 7636
- 29 Iaroshenko VO, Gevorgyan A, Mkrtchyan S, Arakelyan K, Grigoryan T, Yedoyan J, Villinger A, Langer P. J. Org. Chem. 2015; 80: 2103
- 30 Review: Gribble GW. Prog. Heterocycl. Chem. 2020; 31: 83
- 31 Pelkey ET, Gribble GW. Tetrahedron Lett. 1997; 38: 5603
- 32 Ivanov A, Iaroshenko VO, Villinger A, Langer P. Synlett 2015; 26: 2285
- 33 Miliutina M, Ivanov A, Ejaz SA, Iqbal J, Villinger A, Iaroshenko VO, Langer P. RSC Adv. 2015; 5: 60054
- 34a Huse H, Marvin W. Chem. Rev. 2011; 111: 152
- 34b Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
- 34c Han X, Yue Z, Zhang X, He Q, Yang C. J. Org. Chem. 2013; 78: 4850
- 34d Massari S, Daelemans D, Barreca ML, Knezevich A, Sabatini S, Cecchetti V, Marcello A, Pannecouque C, Tabarrini O. J. Med. Chem. 2010; 53: 64
- 34e Messaoudi S, Hamze A, Provot O, Tréguier B, De Losada JR, Bignon J, Liu M.-J, Wdzieczak-Bakala J, Thoret S, Dubois J, Brion J.-D. Alami, ChemMedChem 2011; 6: 488
- 34f Rajabalian S, Foroumadi A, Shafiee A, Emami S. J. Pharm. Pharm. Sci. 2007; 10: 153
- 34g Janin YL. Drug Discovery Today 2010; 15: 342
- 35 Miliutina M, Ejaz SA, Khan SU, Iaroshenko VO, Villinger A, Iqbal J, Langer P. Eur. J. Med. Chem. 2017; 126: 408
- 36 Iqbal J, Ejaz SA, Khan I, Ausekle E, Miliutina M, Langer P. Daru, J. Pharm. Sci. 2019; 27: 613
- 37 Iaroshenko VO, Mkrtchyan S, Villinger A, Langer P. Synthesis 2012; 45: 205
- 38 Mbere JM, Bremner JB, Skelton BW, White AH. Tetrahedron 2011; 67: 6895
- 39 Iaroshenko VO, Ali S, Mkrtchyan S, Gevorgyan A, Babar TM, Semeniuchenko V, Hassan Z, Villinger A, Langer P. Tetrahedron Lett. 2012; 53: 7135
- 40 Iaroshenko VO, Ali S, Babar TM, Abbasi M, Sosnovskikh VY, Villinger A, Langer P. Tetrahedron 2013; 69: 3167
- 41a Miliutina M, Ivon Y, Slobodianiuk Y, Ejaz SA, Iqbal J, Villinger A, Iaroshenko VO, Langer P. Chem. Heterocycl. Compd. 2019; 55: 465
- 41b Tien TA. N, Miliutina M, Radolko J, Thom R, Dang TT, Ehlers P, Langer P. Tetrahedron 2022; 104: 132608
- 42a Kawamura N, Sawa R, Takahashi Y, Isshiki K, Sawa T, Naganawa H, Takeuchi T. J. Antibiot. 1996; 49: 651
- 42b Alberola A, Álvaro R, Ortega AG, Sañudo C. Tetrahedron 1997; 53: 16185
- 42c Shang N.-N, Shao Y.-X, Cai Y.-H, Guan M, Huang M, Cui W, He L, Yu Y.-J, Huang L, Li Z, Bu X.-Z, Ke H, Luo H.-B. Biochem. Pharmacol. 2014; 89: 86
- 42d Shao YX, Huang M, Cui W, Feng LJ, Wu Y, Cai Y, Li Z, Zhu X, Liu P, Wan Y, Ke H, Luo H.-B. J. Med. Chem. 2014; 57: 10304
- 42e Wu D, Zhang T, Chen Y, Huang Y, Geng H, Yu Y, Zhang C, Lai Z, Wu Y, Guo X, Chen J, Luo H.-B. J. Med. Chem. 2017; 60: 6622
- 43a Estrada E, Gómez M, Castañedo N, Pérez C. J. Mol. Struct.: THEOCHEM 1999; 468: 193
- 43b Gonzalez-Diaz H, Agueero G, Cabrera MA, Molina R, Santana L, Uriarte E, Delogu G, Castañedo N. Bioorg. Med. Chem. Lett. 2005; 15: 551
- 44 Dang TT, Dang TT, Langer P. Synlett 2006; 2812
- 45 Langer P. Synlett 2022; 33: 1029
- 46a Ganetsky M, Babu KM, Salhanick SD, Brown RS, Boyer EW. J. Med. Toxicol. 2011; 7: 281
- 46b Zhou Y, Yao Z, Zhu L, Tang Y, Chen J, Wu J. Front. Pharmacol. 2021; 12: 626063
- 47 Hauel NH, Nar H, Priepke H, Ries U, Stassen J.-M, Wienen W. J. Med. Chem. 2002; 45: 1757
- 48 Jopp S, Molenda R, Seiler ER. D, Maitz MF, Villinger A, Ehlers P, Langer P. ChemistrySelect 2019; 4: 13802
Chameleons are animals that can change their colour depending on the environment and situation. The term ‘chemical chameleon’ was recently employed for nitro compounds:
However, the term was suggested for the first time in 1984 by Trost for sulfones serving as 1,1-dipole synthons:
Reviews:
For synthetic work, see:
Reviews:
Reviews: