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 2020; 52(17): 2528-2534
DOI: 10.1055/s-0039-1690886
DOI: 10.1055/s-0039-1690886
paper
Synthesis of a Novel 1,4-Dicarbonyl Scaffold – Ethyl 3-Formyl-4,5-dihydrofuran-2-carboxylate – and Its Application to the Synthesis of Pyridazines
The authors are grateful for financial support from the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS/CNPq – PRONEX – Grant No. 16/2551-0000477-3) and fellowships from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES; M.A.M.) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq; P.A.M., A.F.C.).Further Information
Publication History
Received: 09 January 2020
Accepted after revision: 15 March 2020
Publication Date:
14 April 2020 (online)
Abstract
The 1,4-dicarbonyl scaffold ethyl 3-formyl-4,5-dihydrofuran-2-carboxylate was obtained through the rearrangement of the parent ethyl 2-(4,5-dihydrofuran-3-yl)-2-oxoacetate and applied to the synthesis of a series of 7-alkoxy-2,3-dihydrofuro[2,3-d]pyridazines. Twelve pyridazines were obtained in yields of up to 70%.
Key words
pyridazines - enones - oxoacetates - dihydrofuran - 1,4-dicarbonyl compounds - formyl estersSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690886.
- Supporting Information
-
References
- 1 Zhao P, Wu X, Zhou Y, Geng X, Wang C, Wu Y, Wu A. Org. Lett. 2019; 21: 2708
- 2 Kaldre D, Klose I, Maulide N. Science 2018; 361: 664
- 3 Yetra SR, Patra A, Biju AT. Synthesis 2015; 47: 1357
- 4 Xue S, Li L, Liu Y, Guo Q. J. Org. Chem. 2006; 71: 215
- 5 Parida BB, Das PP, Niocel M, Cha JK. Org. Lett. 2013; 15: 1780
- 6 Esumi N, Suzuki K, Nishimoto Y, Yasuda M. Org. Lett. 2016; 18: 5704
- 7 Liu C, Deng Y, Wang J, Yang Y, Tang S, Lei A. Angew. Chem. Int. Ed. 2011; 50: 7337
- 8 Jang H, Hong J, MacMillan DW. C. J. Am. Chem. Soc. 2007; 129: 7004
- 9 Clift MD, Taylor CN, Thomson RJ. Org. Lett. 2007; 9: 4667
- 10 Robinson EE, Thomson RJ. J. Am. Chem. Soc. 2018; 140: 1956
- 11 Huang S, Kötzner L, De CK, List B. J. Am. Chem. Soc. 2015; 137: 3446
- 12 Konstantinidou M, Kurpiewska K, Kalinowska-Tłuscik J, Doemling A. Eur. J. Org. Chem. 2019; 6714
- 13 Marangoni MA, Bencke CE, Bonacorso HG, Martins MA. P, Zanatta N. Tetrahedron Lett. 2018; 59: 121
- 14 Stepaniuk OO, Rudenko TV, Vashchenko BV, Matvienko VO, Kondratov IS, Tolmachev AA, Grygorenko OO. Tetrahedron 2019; 75: 3472
- 15 Liu Q, Wang L, Kang Q, Zhang XP, Tang Y. Angew. Chem. Int. Ed. 2016; 55: 9220
- 16 Machado P, Lima GR, Rotta M, Bonacorso HG, Zanatta N, Martins MA. P. Ultrason. Sonochem. 2011; 18: 293
- 17 Stepaniuk OO, Matvienko VO, Kondratov IS, Shishkin OV, Volochnyuk DM, Mykhailiuk PK, Tolmachev AA. Synthesis 2012; 44: 895
- 18a Paal C. Chem. Ber. 1884; 17: 2756
- 18b Knorr L. Chem. Ber. 1884; 17: 2863
- 18c For a review, see: Friedrichsen W. Furans and Their Benzo Derivatives: Synthesis, In Comprehensive Heterocyclic Chemistry II, Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; New York: 1996: 351-393
- 19a Paal C. Chem. Ber. 1885; 18: 367
- 19b Knorr L. Chem. Ber. 1885; 18: 299
- 19c For a review, see: Jones RA, Bean GP. The Chemistry of Pyrroles . Academic Press; London: 1977: see pages 51-57 , 74-79 in particular
- 20a Paal C. Chem. Ber. 1885; 18: 2251
- 20b Sonpatki VM, Herbert MR, Sandovoss LM, Seed AJ. J. Org. Chem. 2001; 66: 7283
- 20c Kiryanov AA, Sampson P, Seed A. J. Org. Chem. 2001; 66: 7925
- 21a Grieco PA. J. Org. Chem. 1978; 87: 2363
- 21b Fiandanese V, Marchese G, Naso F. Tetrahedron Lett. 1988; 29: 3587
- 22 Lu P, Mailyan A, Gu Z, Guptill DM, Wang H, Davies HM. L, Zakarian A. J. Am. Chem. Soc. 2014; 136: 17738
- 23 Taber DF, Petty EH, Raman K. J. Am. Chem. Soc. 1985; 107: 196
- 24 Corey EJ, Weinshenker NM, Schaaf TK, Huber W. J. Am. Chem. Soc. 1969; 91: 5675
- 25 Abed HB, Mammoliti O, Bande O, Lommen GV, Herdewijn P. J. Org. Chem. 2013; 78: 7845
- 26 Horak F, Zieglmayer UP. Expert Rev. Clin. Immunol. 2009; 5: 659
- 27 Aleeva GN, Molodavkin GM, Voronina TA. Bull. Exp. Biol. Med. 2009; 148: 54
- 28 Liu B, Zhu F, Huang Y, Wang Y, Yu F, Fan B, Yao J. J. Agric. Food Chem. 2010; 58: 2673
- 29 Abdelghani E, Shehab WS, El-Mobayed M, Hamid AM. A. Int. J. Basic Appl. Sci. 2012; 1: 220
- 30 Fernandes SS. M, de Souza JA, Belsley M, Raposo MM. M. Molecules 2018; 23: 3014
- 31 Nikolaev VA, Cantillo D, Kappe CO, Medvedev JJ, Prakash GK. S, Supurgibekov MB. Chem. Eur. J. 2016; 22: 174
- 32 Komkov AV, Komendantova AS, Menchikov LG, Chernoburova EI, Volkova YA, Zavarzin IV. Org. Lett. 2015; 17: 3734
- 33 Borisov AV, Voloshchuk VV, Nechayev MA, Grygorenko OO. Synthesis 2013; 45: 2413
- 34 Guo R, Mo X, Zhang G. Org. Lett. 2019; 21: 1263
- 35 Machado P, Rosa FA, Rossatto M, Sant’Anna GS, Sauzem PD, Silva RM. S, Rubin MA, Ferreira J, Bonacorso HG, Zanatta N, Martins MA. P. ARKIVOC 2007; (xvi): 281
- 36 Tišler M, Stanovnik B. Adv. Heterocycl. Chem. 1968; 9: 211