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Synthesis 2021; 53(07): 1285-1291
DOI: 10.1055/s-0040-1705940
DOI: 10.1055/s-0040-1705940
paper
Reductive Knoevenagel Condensation with the Zn–AcOH System
Research was supported by the Russian Foundation for Basic Research, grant number 18-03-00549.
Abstract
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn–AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705940.
- Supporting Information
Publication History
Received: 21 May 2020
Accepted after revision: 16 September 2020
Article published online:
29 October 2020
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References
- 1 Shinkai H, Onogi S, Tanaka M, Shibata T, Iwao M, Wakitani K, Uchida I. J. Med. Chem. 1998; 41: 1927
- 2 Griffith D, Morgan MP, Marmion CJ. Chem. Commun. 2009; 6735
- 3 Hayashi Y. Chem. Sci. 2016; 7: 866
- 4 Alexander ER, Cope AC. J. Am. Chem. Soc. 1944; 66: 886
- 5a Goettmann F, Grosso D, Mercier F, Mathey F, Sanchez C. Chem. Commun. 2004; 1240
- 5b Verde-Sesto E, Merino E, Rangel-Rangel E, Corma A, Iglesias M, Sánchez F. ACS Sustain. Chem. Eng. 2016; 4: 1078
- 6a Baidossi M, Joshi AV, Mukhopadhyay S, Sasson Y. Tetrahedron Lett. 2005; 46: 1885
- 6b Motokura K, Fujita N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Tetrahedron Lett. 2005; 46: 5507
- 6c Li P, Liu H, Yu Y, Cao C.-Y, Song W.-G. Chem. Asian J. 2013; 8: 2459
- 6d Li P, Yu Y, Liu H, Cao C.-Y, Song W.-G. Nanoscale 2014; 6: 442
- 6e Patankar SC, Dodiya SK, Yadav GD. J. Mol. Catal. A: Chem. 2015; 409: 171
- 6f Wang H, Wang Y, Jia A, Wang C, Wu L, Yang Y, Wang Y. Catal. Sci. Technol. 2017; 7: 5572
- 7 Abe F, Hayashi T, Tanaka M. Chem. Lett. 1990; 19: 765
- 8a Kolesnikov PN, Usanov DL, Barablina EA, Maleev VI, Chusov D. Org. Lett. 2014; 16: 5068
- 8b Yagafarov NZ, Usanov DL, Moskovets AP, Kagramanov ND, Maleev VI, Chusov D. ChemCatChem 2015; 7: 2590
- 8c Denmark SE, Ibrahim MY. S, Ambrosi A. ACS Catal. 2017; 7: 613
- 8d Muratov K, Kuchuk E, Vellalath S, Afanasyev OI, Moskovets AP, Denisov G, Chusov D. Org. Biomol. Chem. 2018; 16: 7693
- 9 Afanasyev OI, Zarochintsev A, Petrushina T, Cherkasova A, Denisov G, Cherkashchenko I, Chusova O, Jinho O, Man-Seog C, Usanov DL, Semenov SE, Chusov D. Eur. J. Org. Chem. 2019; 32
- 10a Tóth G, Kövér KE. Synth. Commun. 1995; 25: 3067
- 10b Mudhar H, Witty A. Tetrahedron Lett. 2010; 51: 4972
- 10c Sun H, Ye D, Jiang H, Chen K, Liu H. Synthesis 2010; 2577
- 10d Wu J, Jiang H. Synth. Commun. 2011; 41: 1218
- 11a Hrubowchak DM, Smith FX. Tetrahedron Lett. 1983; 24: 4951
- 11b Linton M, Gonzalez J, Li H, Tatlock J, Jewell T, Johnson S, Drowns M, Patel L, Blazel J, Ornelas M. Synthesis 2010; 4015
- 12 Fillion E, Fishlock D. Org. Lett. 2003; 5: 4653
- 13a Dunham JC, Richardson AD, Sammelson RE. Synthesis 2006; 680
- 13b Tayyari F, Wood D, Fanwick P, Sammelson R. Synthesis 2008; 279
- 14 Huang X, Xie L. Synth. Commun. 1986; 16: 1701
- 15 Guyon C, Duclos M.-C, Sutter M, Métay E, Lemaire M. Org. Biomol. Chem. 2015; 13: 7067
- 16a Ramachary DB, Kishor M, Ramakumar K. Tetrahedron Lett. 2006; 47: 651
- 16b Ramachary DB, Venkaiah C, Reddy YV, Kishor M. Org. Biomol. Chem. 2009; 7: 2053
- 16c Ramachary DB, Jain S. Org. Biomol. Chem. 2011; 9: 1277
- 16d Ramachary DB, Venkaiah C, Reddy YV. Org. Biomol. Chem. 2014; 12: 5400
- 16e Peraka S, Hussain A, Ramachary DB. J. Org. Chem. 2018; 83: 9795
- 17a Li J, Liu Q, Xing RG, Shen XX, Liu ZG, Zhou B. Chin. Chem. Lett. 2009; 20: 25
- 17b Yang Y.-Q, Lu Z. Chin. J. Chem. 2014; 32: 650
- 17c He T, Shi R, Gong Y, Jiang G, Liu M, Qian S, Wang Z. Synlett 2016; 27: 1864
- 17d Jiang G, Liu M, Fang D, Tan P, Huang M, Zhou T, Jiang Z, Xu Z, Wang Z. RSC Adv. 2018; 8: 8961
- 17e Kalita S, Deka D. Synlett 2018; 29: 477
- 18 Sakai T, Miyata K, Tsuboi S, Utaka M. Bull. Chem. Soc. Jpn. 1989; 62: 4072
- 19a Schneidewind W. Ber. Dtsch. Chem. Ges. 1888; 21: 1323
- 19b Harries C, Hübner F. Justus Liebigs Ann. Chem. 1897; 296: 295
- 20a Conrad M, Reinbach H. Ber. Dtsch. Chem. Ges. 1901; 34: 1339
- 20b Chukhina EI. Zh. Obshch. Khim. 1958; 28: 2582
- 20c Jursic BS, Stevens ED. Tetrahedron Lett. 2003; 44: 2203
- 20d Milite C, Feoli A, Sasaki K, La Pietra V, Balzano AL, Marinelli L, Mai A, Novellino E, Castellano S, Tosco A, Sbardella G. J. Med. Chem. 2015; 58: 2779
- 20e Smith LI, Dobrovolny FJ. J. Am. Chem. Soc. 1926; 48: 1693
- 20f Yamamura K, Miyake H, Murata I. J. Org. Chem. 1986; 51: 251
- 20g Saha S, Ghosh T, Bandyopadhyay C. Synth. Commun. 2008; 38: 2429
- 20h Sondengam BL, Fomum ZT, Charles G, Akam TM. J. Chem. Soc., Perkin Trans. 1 1983; 1219
- 20i Morel G, Foucaud A. Bull. Soc. Chim. Fr. 1970; 2354
- 20j Mallia CJ, Englert L, Walter GC, Baxendale IR. Beilstein J. Org. Chem. 2015; 11: 875
- 20k Andrés M, Bravo M, Buil MA, Calbet M, Castillo M, Castro J, Eichhorn P, Ferrer M, Lehner MD, Moreno I, Roberts RS, Sevilla S. Eur. J. Med. Chem. 2014; 71: 168
- 21a Ivanov KL, Villemson EV, Latyshev GV, Bezzubov SI, Majouga AG, Melnikov MYa, Budynina EM. J. Org. Chem. 2017; 82: 9537
- 21b Zaytsev SV, Villemson EV, Ivanov KL, Budynina EM, Melnikov MYa. Eur. J. Org. Chem. 2017; 2814
- 22 Ivanov KL, Vatsouro IM, Bezzubov SI, Melnikov MYa, Budynina EM. Org. Chem. Front. 2018; 5: 1655
- 23a Takuwa T, Minowa T, Fujisawa H, Mukaiyama T. Chem. Pharm. Bull. 2005; 53: 476
- 23b Boiadjiev SE, Lightner DA. J. Phys. Org. Chem. 1999; 12: 751
- 23c Leypold M, Wallace PW, Kljajic M, Schittmayer M, Pletz J, Illaszewicz-Trattner C, Guebitz GM, Birner-Gruenberger R, Breinbauer R. Tetrahedron Lett. 2015; 56: 5619
- 23d Buckley TF, Rapoport H. J. Am. Chem. Soc. 1980; 102: 3056
- 23e McBride BJ, Garst ME. Tetrahedron 1993; 49: 2839
- 23f Liu C, Han X, Wang X, Widenhoefer RA. J. Am. Chem. Soc. 2004; 126: 3700
- 23g Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9533
- 23h Somei M, Karasawa Y, Chikara Kaneko A. Heterocycles 1981; 16: 941
- 23i Mu X, Chen S, Zhen X, Liu G. Chem. Eur. J. 2011; 17: 6039
- 23j Liu Y, Mao Y, Hu Y, Gui J, Wang L, Wang W, Zhang S. Adv. Synth. Catal. 2019; 361: 1554