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 2018; 50(04): 872-880
DOI: 10.1055/s-0036-1590947
DOI: 10.1055/s-0036-1590947
paper
Synthesis of Malononitrile-Substituted Diarylmethines via 1,6-Addition of Masked Acyl Cyanides to para-Quinone Methides
Further Information
Publication History
Received: 06 October 2017
Accepted: 09 October 2017
Publication Date:
23 November 2017 (online)
Abstract
An efficient method for the synthesis of malononitrile-substituted diarylmethines through 1,6-conjugate addition of para-quinone methides with masked acyl cyanide (MAC) reagents has been developed. Under mild conditions, the scalable reaction occurs in good to excellent yields providing a straightforward access to a series of malononitrile-substituted diarylmethines. The synthetic utility of this protocol has been demonstrated in the synthesis of bioactive compounds.
Key words
diarylmethines - 1,6-addition - masked acyl cyanides - para-quinone methides - malononitrile-substituted diarylmethinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590947.
- Supporting Information
-
References
- 1a Seebach D. Angew. Chem., Int. Ed. Engl. 1979; 18: 239
- 1b Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1975; 14: 15
- 2a Corey EJ. Seebach D. Angew. Chem., Int. Ed. Engl. 1965; 4: 1075
- 2b Corey EJ. Seebach D. Angew. Chem., Int. Ed. Engl. 1965; 4: 1077
- 2c Seebach D. Corey EJ. J. Org. Chem. 1975; 40: 231
- 4 Brehme R. Enders D. Fernandez R. Lassaletta JM. Eur. J. Org. Chem. 2007; 5629
- 5a Nemoto H. Kubota Y. Yamamoto Y. J. Org. Chem. 1990; 55: 4515
- 5b Nemoto H. Kawamura T. Miyoshi N. J. Am. Chem. Soc. 2005; 127: 14546
- 5c Nemoto H. Ma R. Kawamura T. Kamiya M. Shibuya M. J. Org. Chem. 2006; 71: 6038
- 5d Nemoto H. Ma R. Kawamura T. Yatsuzuka K. Kamiya M. Shibuya M. Synthesis 2008; 3819
- 5e Nemoto H. Kawamura T. Kitasaki K. Yatsuzuka K. Kamiya M. Yoshioka Y. Synthesis 2009; 1694
- 6a Nemoto H. Ma R. Suzuki I. Shibuya M. Org. Lett. 2000; 2: 4245
- 6b Roche SP. Faure S. Aitken DJ. Angew. Chem. Int. Ed. 2008; 47: 6840
- 6c Yamatsugu K. Kanai M. Shibasaki M. Tetrahedron 2009; 65: 6017
- 6d Yamatsugu K. Yin L. Kamijo S. Kimura Y. Kanai M. Shibasaki M. Angew. Chem. Int. Ed. 2009; 48: 1070
- 6e Yang KS. Nibbs AE. Türkmen YE. Rawal VH. J. Am. Chem. Soc. 2013; 135: 16050
- 6f Yang KS. Rawal VH. J. Am. Chem. Soc. 2014; 136: 16148
- 6g Kagawa N. Nibbs AE. Rawal VH. Org. Lett. 2016; 18: 2363
- 6h Hethcox JC. Shockley SE. Stoltz BM. Org. Lett. 2017; 19: 1527
- 7a Biju AT. ChemCatChem 2011; 3: 1847
- 7b Silva EM. P. Silva AM. S. Synthesis 2012; 44: 3109
- 7c Lear MJ. Hayashi Y. ChemCatChem 2013; 5: 3499
- 7d Chauhan P. Kaya U. Enders D. Adv. Synth. Catal. 2017; 359: 888
- 8a Peter MG. Angew. Chem. Int. Ed. 1989; 28: 555
- 8b Toteva MM. Richard JP. Adv. Phys. Org. Chem. 2011; 45: 39
- 8c Parra A. Tortosa M. ChemCatChem 2015; 7: 1524
- 9a Gai K. Fang X. Li X. Xu J. Wu X. Lin A. Yao H. Chem. Commun. 2015; 51: 15831
- 9b López A. Parra A. Jarava-Barrera C. Tortosa M. Chem. Commun. 2015; 51: 17684
- 9c Ramanjaneyulu BT. Mahesh S. Anand RV. Org. Lett. 2015; 17: 3952
- 9d Reddy V. Anand RV. Org. Lett. 2015; 17: 3390
- 9e Yuan Z. Fang X. Li X. Wu J. Yao H. Lin A. J. Org. Chem. 2015; 80: 11123
- 9f Zhang X.-Z. Du J.-Y. Deng Y.-H. Chu W.-D. Yan X. Yu K.-Y. Fan C.-A. J. Org. Chem. 2016; 81: 2598
- 9g Molleti N. Kang JY. Org. Lett. 2017; 19: 958
- 9h Zhang Z.-P. Dong N. Li X. Chem. Commun. 2017; 53: 1301
- 10a Chu W.-D. Zhang L.-F. Bao X. Zhao X.-H. Zeng C. Du J.-Y. Zhang G.-B. Wang F.-X. Ma X.-Y. Fan C.-A. Angew. Chem. Int. Ed. 2013; 52: 9229
- 10b Caruana L. Kniep F. Johansen TK. Poulsen PH. Jørgensen KA. J. Am. Chem. Soc. 2014; 136: 15929
- 10c Jarava-Barrera C. Parra A. López A. Cruz-Acosta F. Collado-Sanz D. Cárdenas DJ. Tortosa M. ACS Catal. 2015; 6: 442
- 10d Lou Y. Cao P. Jia T. Zhang Y. Wang M. Liao J. Angew. Chem. Int. Ed. 2015; 54: 12134
- 10e Wang Z. Wong YF. Sun J. Angew. Chem. Int. Ed. 2015; 54: 13711
- 10f Deng Y.-H. Zhang X.-Z. Yu K.-Y. Yan X. Du J.-Y. Huang H. Fan C.-A. Chem. Commun. 2016; 52: 4183
- 10g Dong N. Zhang Z.-P. Xue X.-S. Li X. Cheng J.-P. Angew. Chem. Int. Ed. 2016; 55: 1460
- 10h He F.-S. Jin J.-H. Yang Z.-T. Yu X. Fossey JS. Deng W.-P. ACS Catal. 2016; 6: 652
- 10i Li X. Xu X. Wei W. Lin A. Yao H. Org. Lett. 2016; 18: 428
- 10j Wong YF. Wang Z. Sun J. Org. Biomol. Chem. 2016; 14: 5751
- 10k Zhang X.-Z. Deng Y.-H. Yan X. Yu K.-Y. Wang F.-X. Ma X.-Y. Fan C.-A. J. Org. Chem. 2016; 61: 5655
- 10l Zhao K. Zhi Y. Wang A. Enders D. ACS Catal. 2016; 6: 657
- 10m Zhao K. Zhi Y. Shu T. Valkonen A. Rissanen K. Enders D. Angew. Chem. Int. Ed. 2016; 55: 12104
- 11a Urbani P. Cascio MG. Ramunno A. Bisogno T. Saturnino C. Di Marzo V. Bioorg. Med. Chem. 2008; 16: 7510
- 11b Tessier P. Leit S. Smil D. Dèziel R. Ajamian A. Chantigny YA. Dominguez C. Patent WO 2008/122115 A1, 2008
- 12 Zhao J. Fan X. Wang S. Li S. Shang S. Yang Y. Xu N. Lü Y. Shi J. J. Nat. Prod. 2004; 67: 1032
- 13 CCDC 1566735 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
For selected examples, see:
For applications of MAC reagents in total synthesis (ref. 6a–d) and recent reports (ref. 6e–h), see:
For selected reviews and highlights on 1,6-addition reactions, see:
For selected reviews on para-quinone methides, see:
For selected reports of non-enantioselective reactions, see:
For selected reports on enantioselective reactions, see: