Assembly of Pyran-Fused Isoquinolines via Rhodium-Catalyzed Double Annulations of Methyl Benzimidates with Diazo Compounds

Abstract

A variety of pyran-fused isoquinoline derivatives were prepared in moderate to good yields through the rhodium-catalyzed dual C–H functionalization/annulation of methyl benzimidates and diazo compounds. A one-pot procedure, broad substrate scope, diversified products, and mild reaction conditions make this transformation a powerful tool for the synthesis of fused heteroarenes. In addition, the synthetic application was extended by large-scale synthesis and late-stage functionalization via Pd-catalyzed Suzuki–Miyaura, Heck, and Sonogashira cross-coupling reactions. Furthermore, a photophysical survey reveals that the pyran-fused isoquinoline products exhibit fluorescence properties and show potential for exploring fluorescent material applications.

Key words

annulations - C–H activation - diazo compounds - isoquinolines - methyl benzimidates

Publikationsverlauf

Eingereicht: 10. April 2022

Angenommen nach Revision: 05. Mai 2022

Accepted Manuscript online:
05. Mai 2022

Artikel online veröffentlicht:
28. Juni 2022

• References


For reviews, see:
• 1a Khan AY, Kumar GS. Biophys. Rev. 2015; 7: 407
• 1b Heravi MM, Nazari N. Curr. Org. Chem. 2015; 19: 2358
• 1c Dembitsky VM, Gloriozova TA, Poroikov VV. Phytomedicine 2015; 22: 183
• 1d Gualandi A, Mengozzi L, Manoni E, Cozzi PG. Catal. Lett. 2015; 145: 398
• 1e He R, Huang Z.-T, Zheng Q.-Y, Wang C. Tetrahedron Lett. 2014; 55: 5705
• 1f Iranshahy M, Quinn RJ, Iranshahi M. RSC Adv. 2014; 4: 15900
• 2a Kartsev VG. Med. Chem. Res. 2004; 13: 325
• 2b Bentley KW. Nat. Prod. Rep. 2006; 23: 444
• 2c Bentley KW. Nat. Prod. Rep. 2004; 21: 395
• 2d Croisy-Delcey M, Croisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg. Med. Chem. 2000; 8: 2629
• 3a Su Y.-J, Huang H.-L, Li C.-L, Chien C.-H, Tao Y.-T, Chou P.-T, Datta S, Liu R.-S. Adv. Mater. 2003; 15: 884
• 3b Ho C.-L, Wong W.-Y, Gao Z.-Q, Chen C.-H, Cheah K.-W, Yao B, Xie Z, Wang Q, Ma D, Wang L, Yu X.-M, Kwok H.-S, Lin Z. Adv. Funct. Mater. 2008; 18: 319
• 4a Ansari AJ, Joshi G, Sharma P, Maurya AK, Metre RK, Agnihotri VK, Chandaluri CG, Kumar R, Singh S, Sawant DM. J. Org. Chem. 2019; 84: 3817
• 4b Huang J, Fu Y, Deng Z, Chen W, Song Z, Peng Y. Org. Biomol. Chem. 2020; 18: 9863
• 5a Bentley KW. Nat. Prod. Rep. 2005; 22: 249
• 5b Chrzanowska M, Rozwadowska MD. Chem. Rev. 2004; 104: 3341
• 5c Sonawane AD, Sonawane RA, Win KM. N, Ninomiya M, Koketsu M. Org. Biomol. Chem. 2020; 18: 2129
• 6 Wu X, Xiong H, Sun S, Cheng J. Org. Lett. 2018; 20: 1396
• 7 Shankar M, Ghosh K, Mukherjee K, Rit RK, Sahoo AK. Org. Lett. 2018; 20: 5144
• 8 Li J, Liu J, Yin J, Zhang Y, Han W, Lan J, Wu D, Bin Z, You J. J. Org. Chem. 2019; 84: 15697
• 9 Mayakrishnan S, Tamizmani M, Maheswari NU. Chem. Commun. 2020; 56: 15462

For C–H activation/N-cyclization, see:
• 10a Li J, Tang M, Zang L, Zhang X, Zhang Z, Ackermann L. Org. Lett. 2016; 18: 2742
• 10b Wu Y, Sun P, Zhang K, Yang T, Yao H, Lin A. J. Org. Chem. 2016; 81: 2166
• 10c Mahesha CK, Agarwal DS, Karishma P, Markad D, Mandal SK, Sakhuja R. Org. Biomol. Chem. 2018; 16: 8585
• 10d Li B, Zhang B, Zhang X, Fan X. Chem. Commun. 2017; 53: 1297
• 10e Karishma P, Mahesha CK, Agarwal DS, Mandal SK, Sakhuja R. J. Org. Chem. 2018; 83: 11661
• 10f Hu W, He X, Zhou T, Zuo Y, Zhang S, Yang T, Shang Y. Org. Biomol. Chem. 2021; 19: 552
• 10g Ning Y, He X, Zuo Y, Wang J, Tang Q, Xie M, Li R, Shang Y. Org. Biomol. Chem. 2020; 18: 2893
• 10h Zuo Y, He X, Ning Y, Wu Y, Shang Y. J. Org. Chem. 2018; 83: 13463

For C–H actiation/O-cyclization, see:
• 11a Li XG, Sun M, Liu K, Jin Q, Liu PN. Chem. Commun. 2015; 51: 2380
• 11b Yang C, Chen C, Li S, He X, Zuo Y, Hu W, Zhou T, Wang J, Shang Y. Org. Lett. 2020; 22: 2506
• 11c Yao J, Kong L, Li X. Chem. Commun. 2020; 56: 13169
• 11d Yang C, He X, Zhang L, Han G, Zuo Y, Shang Y. J. Org. Chem. 2017; 82: 2081
• 11e Zuo Y, He X, Ning Y, Zhang L, Wu Y, Shang Y. New J. Chem. 2018; 42: 1673

For double C–H activation/cyclization, see:
• 12a Fang F, Zhang C, Zhou C, Li Y, Zhou Y, Liu H. Org. Lett. 2018; 20: 1720
• 12b Li S.-S, Xia Y.-Q, Hu F.-Z, Liu C.-F, Su F, Dong L. Chem. Asian J. 2016; 11: 3165
• 12c Xie Y, Chen X, Liu X, Su S.-J, Li J, Zeng W. Chem. Commun. 2016; 52: 5856
• 12d Zhang B, Li B, Zhang X, Fan X. Org. Lett. 2017; 19: 2294
• 12e Yan K, Li B, Wang B. Adv. Synth. Catal. 2018; 360: 2272
• 12f Zhang B, Li B, Guo C, Zhang X, Fan X. Tetrahedron Lett. 2018; 59: 3094
• 13a Song G, Chen D, Pan C.-L, Crabtree RH, Li X. J. Org. Chem. 2010; 75: 7487
• 13b Jiang B, Wu S, Zeng J, Yang X. Org. Lett. 2018; 20: 6573
• 13c Tanaka R, Tanimoto I, Kojima M, Yoshino T, Matsunaga S. J. Org. Chem. 2019; 84: 13203
• 14a Yang X, Jie J, Li H, Piao M. RSC Adv. 2016; 6: 57371
• 14b Li C, Xu H.-B, Zhang J, Liu M, Dong L. Org. Biomol. Chem. 2020; 18: 1412
• 14c Wu B, Yang Z, Zhang H, Wang L, Cui X. Chem. Commun. 2019; 55: 4190
• 14d Wang J, Zha S, Chen K, Zhang F, Zhu J. Org. Biomol. Chem. 2016; 14: 4848
• 14e Li XG, Sun M, Jin Q, Liu K, Liu PN. J. Org. Chem. 2016; 81: 3901
• 15a He X, Zhou Y, Shang Y, Yang C, Zuo Y. ACS Omega 2016; 1: 1277
• 15b He X, Yu Z, Zuo Y, Yang C, Shang Y. Org. Biomol. Chem. 2017; 15: 7127
• 15c Ning Y, He X, Zuo Y, Cai P, Xie M, Wang J, Shang Y. Adv. Synth. Catal. 2019; 361: 3518
• 16 CCDC 2130297 (3aa) 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/structures.
• 17a Li Z, Xie J, Lu P, Wang Y. J. Org. Chem. 2020; 85: 5525
• 17b Kong W.-J, Finger LH, Messinis AM, Kuniyil R, Oliveira JC. A, Ackermann L. J. Am. Chem. Soc. 2019; 141: 17198