Application of Benzofuran-Derived Azadienes as Two-Carbon Building Blocks in Annulations: Chemo- and Diastereoselective Construction of Spiro-Benzofuran Scaffolds

Ye-Xin Wang; Yi-Nan Lu; Lin-Lin Xu; Feng-Tao Sheng; Jin-Peng Zhang; Wei Tan; Feng Shi

doi:10.1055/s-0040-1707205

Synthesis, Table of Contents

Synthesis 2020; 52(20): 2979-2986
DOI: 10.1055/s-0040-1707205

paper

Application of Benzofuran-Derived Azadienes as Two-Carbon Building Blocks in Annulations: Chemo- and Diastereoselective Construction of Spiro-Benzofuran Scaffolds

Ye-Xin Wang

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: wtan@jsnu.edu.cn

,

Yi-Nan Lu

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: wtan@jsnu.edu.cn

,

Lin-Lin Xu

^bKey Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China Email: xiaopangpeng@126.com

,

Feng-Tao Sheng

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: wtan@jsnu.edu.cn

,

Jin-Peng Zhang∗

^bKey Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China Email: xiaopangpeng@126.com

,

Wei Tan∗

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: wtan@jsnu.edu.cn

,

Feng Shi ∗

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China Email: fshi@jsnu.edu.cn Email: wtan@jsnu.edu.cn

› Author Affiliations

Abstract

All articles of this category

§ These authors contributed equally to this work.

Abstract

A base-promoted (2+4) annulation of benzofuran-derived azadienes with para-quinone methide derivatives has been established, which afforded spiro-benzofuran derivatives in generally high yields (57–97%) and with good diastereoselectivities (85:15 to >95:5 dr). This reaction not only represents the first application of benzofuran-derived azadienes as two-carbon building blocks in annulations, but also provides an efficient protocol for the construction of spiro-benzofuran scaffolds with chemoselectivity and high diastereoselectivity. This approach will enrich the chemistry of benzofuran-derived azadiene-involved reactions.

Key words

benzofuran-derived azadiene - para-quinone methide - annulation - spiro-benzofuran - diastereoselectivity

Full Text

References

References

For some reviews:

1a Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
1b Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
1c Wu H, He Y.-P, Shi F. Synthesis 2015; 47: 1990
1d Mei G.-J, Shi F. Chem. Commun. 2018; 54: 6607
1e Wan Y, Li Y, Yan C, Yan M, Tang Z. Eur. J. Med. Chem. 2019; 183: 111691

For some reviews:

2a Mei G.-J, Shi F. Synlett 2016; 27: 2515
2b Mei G.-J, Shi F. J. Org. Chem. 2017; 82: 7695
2c Yan J, Ji X, Hua S, Wang J. Chin. J. Org. Chem. 2018; 38: 791
2d Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
2e Cerveri A, Bandini M. Chin. J. Chem. 2020; 38: 287
2f Tan B. Chin. J. Org. Chem. 2020; 40: 1404

3 For an early report: Rong Z.-Q, Wang M, Chow CH. E, Zhao Y. Chem. Eur. J. 2016; 22: 9483

For (4+1) annulation:

4a Wang C.-S, Li T.-Z, Cheng Y.-C, Zhou J, Mei G.-J, Shi F. J. Org. Chem. 2019; 84: 3214
4b Chen T, Zhang Y, Fu Z, Huang W. Asian J. Org. Chem. 2019; 8: 2175

For (4+2) annulation:

5a Gu Z, Wu B, Jiang G.-F, Zhou Y.-G. Chin. J. Chem. 2018; 36: 1130
5b Fan T, Zhang Z.-J, Zhang Y.-C, Song J. Org. Lett. 2019; 21: 7897
5c Li X, Yan J, Qin J, Lin S, Chen W, Zhan R, Huang H. J. Org. Chem. 2019; 84: 8035
5d Xie H.-P, Sun L, Wu B, Zhou Y.-G. J. Org. Chem. 2019; 84: 15498
5e Marques A.-S, Duhail T, Marrot J, Chataigner I, Coeffard V, Vincent G, Moreau X. Angew. Chem. Int. Ed. 2019; 58: 9969
5f Qi J, Tang H, Chen C, Cui S, Xu G. Org. Chem. Front. 2019; 6: 2760
5g Frankowski S, Skrzyńska A, Sieroń L, Albrecht Ł. Adv. Synth. Catal. 2020;

For (4+3) annulation:

6a Chen J, Huang Y. Org. Lett. 2017; 19: 5609
6b Gao Z.-H, Chen K.-Q, Zhang Y, Kong L.-M, Li Y, Ye S. J. Org. Chem. 2018; 83: 15225
6c Chen J, Jia P, Huang Y. Org. Lett. 2018; 20: 6715
6d Chen K.-Q, Gao Z.-H, Ye S. Org. Chem. Front. 2019; 6: 405
6e Trost BM, Zuo Z. Angew. Chem. Int. Ed. 2020; 59: 1243
6f Liu Y.-Z, Wang Z, Huang Z, Zheng X, Yang W.-L, Deng W.-P. Angew. Chem. Int. Ed. 2020; 59: 1238
6g Kumari P, Liu W, Wang C.-J, Dai J, Wang M.-X, Yang Q.-Q, Deng Y.-H, Shao Z. Chin. J. Chem. 2020; 38: 151

7 For (4+4) annulation: Ni H, Tang X, Zheng W, Yao W, Ullah N, Lu Y. Angew. Chem. Int. Ed. 2017; 56: 14222

For (4+5) annulation:

8a Yang L.-C, Rong Z.-Q, Wang Y.-N, Tan ZY, Wang M, Zhao Y. Angew. Chem. Int. Ed. 2017; 56: 2927
8b Rong Z.-Q, Yang L.-C, Liu S, Yu Z, Wang Y.-N, Tan ZY, Huang R.-Z, Lan Y, Zhao Y. J. Am. Chem. Soc. 2017; 139: 15304

9 For (4+6) annulation: Wang Y.-N, Yang L.-C, Rong Z.-Q, Liu T.-L, Liu R, Zhao Y. Angew. Chem. Int. Ed. 2018; 57: 1596
10 For other annulations: Zeng R, Shan C, Liu M, Jiang K, Ye Y, Liu T.-Y, Chen Y.-C. Org. Lett. 2019; 21: 2312

For 1,4-addition:

11a Gu Z, Zhou J, Jiang G.-F, Zhou Y.-G. Org. Chem. Front 2018; 5: 1148
11b Gu Z, Xie J.-J, Jiang G.-F, Zhou Y.-G. Asian J. Org. Chem. 2018; 7: 1561
11c Lin W, Zhang C, Xu W, Cheng Y, Li P, Li W. Adv. Synth. Catal. 2019; 361: 476
11d Lin W, Lin X, Cheng Y, Chang X, Zhou S, Li P, Li W. Org. Chem. Front. 2019; 6: 2452
11e Xie H.-P, Wu B, Wang X.-W, Zhou Y.-G. Chin. J. Catal. 2019; 40: 1566
11f Zhang C, Cheng Y, Li F, Luan Y, Li P, Li W. Adv. Synth. Catal. 2020; 362: 1286
11g Wang C, Yang Q, Wang M, Shang Y, Tong X, Deng Y, Shao Z. Org. Chem. Front. 2020; 7: 609
11h Hu D, Gao Y, Song X, Du W, Chen Y.-C. Eur. J. Org. Chem. 2020; 514
11i Xie H.-P, Wu B, Chen M.-W, Yu C.-B, Li H.-W, Li X, Zhou Y.-G. Chin. J. Org. Chem. 2020;

For some examples:

12a Kawada M, Watanabe M, Okamoto K, Sugihara H, Hirata T, Maki Y, Imada I, Sanno Y. Chem. Pharm. Bull. 1984; 32: 3532
12b Youssefyeh RD, Campbell HF, Klein S, Airey JE, Darkes P, Powers M, Schnapper M, Neuenschwander K, Fitzpatrick LR. J. Med. Chem. 1992; 35: 895
12c Braun M, Hessamian-Alinejad A, de Lacroix BF, Alvarez BH, Fischer G. Molecules 2008; 13: 995
12d Larghi EL, Kaufman TS. ARKIVOC 2011; (vii): 49

13a Zhang H.-H, Wang C.-S, Li C, Mei G.-J, Li Y, Shi F. Angew. Chem. Int. Ed. 2017; 56: 116
13b Ma C, Jiang F, Sheng F.-T, Jiao Y, Mei G.-J, Shi F. Angew. Chem. Int. Ed. 2019; 58: 3014
13c Wang C.-S, Li T.-Z, Liu S.-J, Zhang Y.-C, Deng S, Jiao Y, Shi F. Chin. J. Chem. 2020; 38: 543
13d Sheng F.-T, Li Z.-M, Zhang Y.-Z, Sun L.-X, Zhang Y.-C, Tan W, Shi F. Chin. J. Chem. 2020; 38: 583

For some reviews on p-QMs:

14a Caruana L, Fochi M, Bernardi L. Molecules 2015; 20: 11733
14b Parra A, Tortosa M. ChemCatChem 2015; 7: 1524
14c Chauhan P, Kaya U, Enders D. Adv. Synth. Catal. 2017; 359: 888
14d Li W, Xu X, Zhang P, Li P. Chem. Asian J. 2018; 13: 2350
14e Lima CG. S, Pauli FP, Costa DC. S, de Souza AS, Forezi LS. M, Ferreira VF, da Silva FC. Eur. J. Org. Chem. 2020; 2650

For catalytic asymmetric (4+1) annulations:

15a Liu L, Yuan Z, Pan R, Zeng Y, Lin A, Yao H, Huang Y. Org. Chem. Front. 2018; 5: 623
15b Zielke K, Kovac O, Winter M, Pospisil J, Waser M. Chem. Eur. J. 2019; 25: 8163
15c Lu H, Zhang H.-X, Tan C.-Y, Liu J.-Y, Wei H, Xu P.-F. J. Org. Chem. 2019; 84: 10292
15d Tan J.-P, Yu P, Wu J.-H, Chen Y, Pan J, Jiang C, Ren X, Zhang H.-S, Wang T. Org. Lett. 2019; 21: 7298

For catalytic asymmetric (4+2) annulations:

16a Zhao K, Zhi Y, Shu T, Valkonen A, Rissanen K, Enders D. Angew. Chem. Int. Ed. 2016; 55: 12104
16b Zhang L, Liu YK, Liu Z, He N, Li W. Org. Biomol. Chem. 2017; 15: 8743
16c Zhang L, Zhou X, Li P, Liu Z, Liu Y, Sun Y, Li W. RSC Adv. 2017; 7: 39216
16d Zhang Z.-P, Xie K.-X, Yang C, Li M, Li X. J. Org. Chem. 2018; 83: 364
16e Jiang X.-L, Wu S.-F, Wang J.-R, Mei G.-J, Shi F. Adv. Synth. Catal. 2018; 360: 4225
16f Yang G.-H, Zhao Q, Zhang Z.-P, Zheng H.-L, Chen L, Li X. J. Org. Chem. 2019; 84: 7883
16g Tan J.-P, Zhang H, Jiang Z, Chen Y, Ren X, Jiang C, Wang T. Adv. Synth. Catal. 2020; 362: 1058
16h Zhao M.-X, Xiang J, Zhao Z.-Q, Zhao X.-L, Shi M. Org. Biomol. Chem. 2020; 18: 1637

For racemic (4+2) annulations:

16i Mei G.-J, Xu S.-L, Zheng W.-Q, Bian C.-Y, Shi F. J. Org. Chem. 2018; 83: 1414
16j Zhou J.-Y, Ma C, Zhang Y.-Z, Wu Q, Shi F. Org. Biomol. Chem. 2018; 16: 9382
16k Cao Z, Zhou G.-X, Ma C, Jiang K, Mei G.-J. Synthesis 2018; 50: 1307
16l Yuan F.-R, Jiang F, Chen K.-W, Mei G.-J, Wu Q, Shi F. Org. Biomol. Chem. 2019; 17: 2361

For catalytic asymmetric (4+3) annulations:

17a Li W, Yuan H, Liu Z, Zhang Z, Cheng Y, Li P. Adv. Synth. Catal. 2018; 360: 2460
17b Liu Q, Li S, Chen X.-Y, Rissanen K, Enders D. Org. Lett. 2018; 20: 3622
17c Jiang F, Yuan F.-R, Jin L.-W, Mei G.-J, Shi F. ACS Catal. 2018; 8: 10234
17d Sun M, Ma C, Zhou S.-J, Lou S.-F, Xiao J, Jiao Y, Shi F. Angew. Chem. Int. Ed. 2019; 58: 8703
17e Liu L, Zhang J. Chin. J. Org. Chem. 2019; 39: 3308

For reviews:

18a Harmata M. Chem. Commun. 2010; 46: 8904
18b Harmata M. Chem. Commun. 2010; 46: 8886
18c Lohse AG, Hsung RP. Chem. Eur. J. 2011; 17: 3812
18d Lam H, Lautens M. Synthesis 2020;

1919

19a CCDC 2007585 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.
19b See the Supporting Information for details.

Supplementary Material