Annulation Reactions of Isoquinolinium Ylides with Sulfamate-Derived Cyclic Imines toward Polycyclic 1,3-Benzoxazepine Heterocycles

This article is dedicated to Prof. H. Ila on the occasion of her 80^th birthday.

Abstract

A dearomatization-guided and (3+2) cycloaddition-triggered annulation reaction of in situ formed isoquinolinium ylides with sulfamate-derived cyclic imines is reported, offering a cogent synthesis of tetracyclic 1,3-benzoxazepine frameworks in high yields. The protocol features successive ring-forming and ring-breaking events in a cascade fashion and is also scalable.

Key words

cascade annulation - dearomatization - benzoxazepines - (3+2) cycloaddition - heterocycles

Publication History

Received: 29 May 2024

Accepted after revision: 20 June 2024

Accepted Manuscript online:
20 June 2024

Article published online:
11 July 2024

• References

• 1a Kapur S, Cho R, Jones C, McKay G, Zipursky RB. Biol. Psychiatry 1999; 45: 1217
• 1b Wong YC, Wo SK, Zuo Z. J. Pharm. Biomed. Anal. 2012; 58: 83
• 1c Popp TA, Tallant C, Rogers C, Fedorov O, Brennan PE, Müller S, Knapp S, Bracher F. J. Med. Chem. 2016; 59: 8889
• 1d Klug DM, Tschiegg L, Diaz R, Rojas-Barros D, Perez-Moreno G, Ceballos G, García-Hernández R, Martinez-Martinez MS, Manzano P, Ruiz LM, Caffrey CR, Gamarro F, Pacanowska DG, Ferrins L, Navarro M, Pollastri MP. J. Med. Chem. 2020; 63: 2527

For reviews, see:
• 2a Kwiecień H, Śmist M, Wrześniewska A. Curr. Org. Synth. 2012; 9: 828
• 2b Lévai A. Heterocycles 2008; 75: 2155
• 3a Miki T, Kori M, Mabuchi H, Tozawa R.-i, Nishimoto T, Sugiyama Y, Teshima K, Yukimasa H. J. Med. Chem. 2002; 45: 4571
• 3b Thansandote P, Chong E, Feldmann KO, Lautens M. J. Org. Chem. 2010; 75: 3495
• 3c Ji F, Lv M.-F, Yi W.-b, Cai C. Adv. Synth. Catal. 2013; 355: 3401
• 3d Zhao H, Meng X, Huang Y. Chem. Commun. 2013; 49: 10513
• 3e Shen J, Xue L, Lin X, Cheng G, Cui X. Chem. Commun. 2016; 52: 3292
• 3f Oshimoto K, Zhou B, Tsuji H, Kawatsura M. Org. Biomol. Chem. 2020; 18: 415
• 4a Cul A, Pesquet A, Daïch A, Chihab-Eddine A, Marchalín S. J. Heterocycl. Chem. 2003; 40: 499
• 4b Ulmer A, Brunner C, Arnold AM, Pöthig A, Gulder T. Chem. Eur. J. 2016; 22: 3660
• 4c Reddy MK, Bhajammanavar V, Baidya M. Org. Lett. 2021; 23: 3868

For a review, see:
• 5a Ghosh P, Mondal SL, Baidya M. Synthesis 2022; 54: 1043

For selected papers, see:
• 5b Ramakrishna I, Ramaraju P, Baidya M. Org. Lett. 2018; 20: 1023
• 5c Mallik S, Bhajammanavar V, Mukherjee AP, Baidya M. Org. Lett. 2019; 21: 2352
• 5d Mallik S, Bhajammanavar V, Baidya M. Org. Lett. 2020; 22: 1437
• 5e Mondal SL, Bhajammanavar V, Ramakrishna I, Baidya M. Chem. Commun. 2023; 59: 13211

For selected annulation reactions with sulfamate-derived cyclic imines, see:
• 6a Liu Y, Kang T.-R, Liu Q.-Z, Chen L.-M, Wang Y.-C, Liu J, Xie Y.-M, Yang J.-L, He L. Org. Lett. 2013; 15: 6090
• 6b Kim H, Kim Y, Kim S.-G. J. Org. Chem. 2017; 82: 8179
• 6c Wu Y, Yuan C, Wang C, Mao B, Jia H, Gao X, Liao J, Jiang F, Zhou L, Wang Q, Guo H. Org. Lett. 2017; 19: 6268
• 6d Mao B, Shi W, Liao J, Liu H, Zhang C, Guo H. Org. Lett. 2017; 19: 6340
• 6e Zhao Z, Yang XX, Ran GY, Ouyang Q, Du W, Chen YC. Org. Lett. 2021; 23: 4791
• 6f Chauhan S, Kumar AS, Swamy KC. K. J. Org. Chem. 2023; 88: 12432

For the formation of NH=SO₂, see:
• 7a Sguazzin MA, Johnson JW, Magolan J. Org. Lett. 2021; 23: 3373
• 7b Our attempts to characterize HN=SO₂ have been unsuccessful so far.