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-00000084.xml
Synthesis 2013; 45(10): 1333-1340
DOI: 10.1055/s-0033-1338298
DOI: 10.1055/s-0033-1338298
paper
Studies on Pyrrolidinones: Chemistry of Dimethoxytriazines
Further Information
Publication History
Received: 30 January 2013
Accepted after revision: 11 March 2013
Publication Date:
28 March 2013 (online)
Abstract
The synthesis of dimethoxytriazine-containing N-aryl substituted pyrrolidinones is realized for the first time. Three new modes of reactivity for these substrates possessing a 4,6-dimethoxy-1,3,5-triazine unit are discussed. Their treatment with acid leads to complete O-demethylation of the methoxy groups, while similar reaction in a basic medium leads to partial O-demethylation. In contrast, heating in the presence of dimethyl sulfate as the catalyst induces migration of the methyl groups from the oxygen atoms to the triazine nitrogens (Hilbert–Johnson transposition). These new scaffolds may demonstrate biological potential.
-
References
- 1a Baldaniya BB, Patel PK. E-J. Chem. 2009; 6: 673
- 1b Almeida L, Aquila B, Chuaqui CE, Guan HP, Huang S, Ioannidis S, Lamb M, Peng B, Shi J, Su M, Su QB. WO2009016410, 2009 ; Chem. Abstr. 2010, 153, 456713.
- 1c Niyaz NM, Guenthenspberger KA, Hunter R, Brown AV, Nugent JS. US 20090093481, 2009 ; Chem. Abstr. 2009, 150, 398582.
- 1d Liu B, Lee Y, Zou JM, Petrassi HM, Joseph RW, Chao WC, Michelotti EL, Bukhtiyarova M, Springman EB, Dorsey BD. Bioorg. Med. Chem. Lett. 2010; 20: 6592
- 1e Solankee A, Kapadia K, Ciric A, Sokovic M, Doytchinova I, Geronikaki A. Eur. J. Med. Chem. 2010; 45: 510
- 1f Pareek PK, Mithlesh Pareek D, Chaudhary M, Pareek A, Kant R, Ojha KG. Main Group Chem. 2011; 10: 63
- 1g Ojha H, Gahlot P, Tiwari AK, Pathak M, Kakkar R. Chem. Biol. Drug Des. 2011; 77: 57
- 1h Fanelli C, Fabbri AA, Monti S, Menicagli R, Pini D, Rapaccini SM, Samaritani S, Salvadori P Presented at the 7th International Congress of Plant Pathology, Edinburgh, Scotland, August 9–16, 1998; British Society for Plant Pathology: Birmingham (UK), 1998, Abstr. 5.6.8.
- 1i Samaritani S, Fabbri AA, Fanelli C, Menicagli R, Salvadori P. Presented at the XXV Convegno Nazionale della Divisione di Chimica Organica, Folgaria, Italy. September 8–12, 1998 Società Chimica Italiana (Divisione di Chimica Organica); Rome: 1998. Abstr. p. P124 (Vol. 1)
- 1j Ricelli A, Fabbri AA, Fanelli C, Menicagli R, Samaritani S, Pini D, Rapaccini SM, Salvadori P. Restaurator 1999; 97
- 2a Singhal GH, Roebke H. DE 2115318, 1971 ; Chem. Abstr. 1972, 76, 72560.
- 2b Just M, Glase I. DD 248590, 1987 ; Chem. Abstr. 1988, 108, 131864.
- 2c Koizumi K, Yamashita O, Wakabayashi K, Tomono K, Sasayama H. WO 9720825, 1997 ; Chem. Abstr. 1997, 127, 95296.
- 2d Gajare AS, Bhawsar SB, Shinde DB, Shingare MS. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1998; 37: 510
- 3a Zhao H, Liu Y, Cui Z, Beattie D, Gu Y, Wang Q. J. Agric. Food Chem. 2011; 59: 11711
- 3b Abell LM, Schloss JV, Rendina AR. Target-site Directed Herbicide Design, ACS Symposium Series No. 524. American Chemical Society; Washington DC: 1993: 16
- 3c Triazine Herbicides: Risk Assessments, ACS Symposium Series No. 524. Ballantine L, McFarland J, Hackett D. American Chemical Society; Washington DC: 1998: xi
- 4a Rigo B, Lespagnol C, Pauly M. J. Heterocycl. Chem. 1986; 23: 183
- 4b Laboratoires PaulyM. EP 135144, 1985 ; Chem. Abstr. 1985, 103, 123914.
- 5 Cauliez P, Couturier D. J. Heterocycl. Chem. 1993; 30: 921
- 6 Oudir S, Rigo B, Hénichart J.-P, Gautret P. Synthesis 2006; 2845
- 7a Menicagli R, Samaritani S, Zucchelli V. Tetrahedron 2000; 56: 9705
- 7b Menicagli R, Samaritani S, Gori S. Tetrahedron Lett. 1999; 40: 8419
- 7c Samaritani S, Menicagli R. Tetrahedron 2002; 58: 1381
- 7d Menicagli R, Samaritani S, Signore G, Vaglini F, Dalla Via L. J. Med. Chem. 2004; 47: 4649
- 7e Courme C, Gillon S, Gresh N, Vidal M, Garbay C, Florent J.-C, Bertounesque E. Tetrahedron Lett. 2008; 49: 4542
- 8a Rembarz G, Fischer E, Roeber KCh, Ohff R, Crahmer H. J. Prakt. Chem. 1969; 311: 889
- 8b Chiang GC. US Patent 4933450, 1990 ; Chem. Abstr. 1990, 113, 231414.
- 8c Gates PS, Jones GP, Saunders DE. WO9309099, 1993 ; Chem. Abstr. 1993, 119, 180810.
- 8d Voss O, Dudfield PJ, Bauer K, Bieringer H, Rosinger C, Ford MJ, Green D. DE 19521355, 1996 ; Chem. Abstr. 1997, 126, 144293.
- 8e Weiss S, Krommer H. US Patent 6342600, 2002 ; Chem. Abstr. 2002, 136, 134795.
- 9 The synthesis of the mixed anhydride of N-methylenedioxy-benzyl pyroglutamic acid and trifluoroacetic acid has been described previously, see: Bourry A, Akue-Gedu R, Rigo B, Hénichart J.-P, Sanz G, Couturier D. J. Heterocycl. Chem. 2003; 40: 989
- 10 Ghinet A, Oudir S, Hénichart J.-P, Rigo B, Pommery N, Gautret P. Tetrahedron 2010; 66: 215
- 11 Cauliez P, Rigo B, Fasseur D, Couturier D. J. Heterocycl. Chem. 1991; 28: 1143
- 12 Thurston JT, Schaefer FC, Dudley JR, Holm-Hansen D. J. Am. Chem. Soc. 1951; 73: 2992
- 13a Azev YA, Dülcks T, Gabel D. Tetrahedron Lett. 2003; 44: 8689
- 13b Azev YA, Gabel D, Dulks T, Shorshnev SV, Klyuev NA. Pharm. Chem. J. 2004; 38: 197
- 14 Pomeisi K, Holy A, Pohl R, Horska K. Tetrahedron 2009; 65: 8486
- 15a Kraljevic TG, Kristafor S, Suman L, Kralj M, Ametamey SM, Cetina M, Raic-Malic S. Bioorg. Med. Chem. 2010; 18: 2704
- 15b Kraljevic TG, Petrovic M, Kristafor S, Makuc D, Plavec J, Ross TL, Ametamey SM, Raic-Malic S. Molecules 2011; 16: 5113
- 16a Prekupec S, Makuc D, Plavec J, Suman L, Kralj M, Pavelic K, Balzarini J, De Clercq E, Mintas M, Raic-Malic S. J. Med. Chem. 2007; 50: 3037
- 16b Mitchell ML, Son JC, Guo H, Im Y.-A, Cho EJ, Wang J, Hayes J, Wang M, Paul A, Lansdon EB, Chen JM, Graupe D, Rhodes G, He G.-X, Geleziunas R, Xu L, Kim CU. Bioorg. Med. Chem. Lett. 2010; 20: 1589
- 17a Khan MW, Kundu NG. J. Chem. Res., Synop. 1999; 20
- 17b Tang J, Maddali K, Dreis CD, Sham YY, Vince R, Pommier Y, Wang Z. Bioorg. Med. Chem. Lett. 2011; 21: 2400
- 18 Nencka R, Votruba I, Hrebabecky H, Jansa P, Tloust’ova E, Horska K, Masojidkova M, Holy A. J. Med. Chem. 2007; 50: 6016
- 19 Katritzky AR, Popp FD, Waring AJ. J. Chem. Soc. B 1966; 565
- 20 Wong JL, Fuchs DS. J. Org. Chem. 1970; 35: 3786
- 21 Newkome GR, Nayak A, Otemaa J, Van D A, Benton WH. J. Org. Chem. 1978; 43: 3362
- 22a Kato T, Oda N, Ito I. Chem. Pharm. Bull. 1977; 25: 215
- 22b Schaefer FC, Dudley JR, Thurston JT. J. Am. Chem. Soc. 1951; 73: 3004
- 23 Hilbert GE, Johnson TB. J. Am. Chem. Soc. 1930; 52: 2001
- 24 Das P, Kundu NG. J. Chem. Res., Synop. 1996; 298
- 25 Piskala A. Tetrahedron Lett. 1964; 5: 2587
- 26 Zimin MG, Fomakhin EV, Gol’dfarb EI, Pudovik AN. Zh. Obshch. Khim. 1986; 56: 553 ; Chem. Abstr. 1987, 106, 102397