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Synthesis of 3a,7a‐Dihydroindoles via Rhodium‐catalyzed Intermolecular Formal [3 + 2] Transannulation Reactions of Triazoles with Alkyl‐substituted Benzene Derivatives 원문보기

Bulletin of the Korean chemical society, v.38 no.11, 2017년, pp.1299 - 1305  

Kim, Hyunseok (Department of Chemistry Kangwon National University Chuncheon 24341 Republic of Korea) ,  Kim, Sun‐Eung (Department of Chemistry Kangwon National University Chuncheon 24341 Republic of Korea) ,  Jeon, Woo Hyung (Department of Chemistry Kangwon National University Chuncheon 24341 Republic of Korea) ,  Lee, Kooyeon (Department of Bio‐) ,  Lee, Phil Ho (Health Technology Kangwon National University Chuncheon 24341 Republic of Korea)

Abstract AI-Helper 아이콘AI-Helper

A synthetic method for a variety of 3a,7a‐dihydroindoles was demonstrated from Rh‐catalyzed intermolecular formal [3 + 2] transannulation reaction of 4‐aryl‐1‐sulfonyl‐1H‐1,2,3‐triazoles with alkyl‐substituted benzene derivatives under m...

참고문헌 (52)

  1. Yoo, Eun Jeong, Ahlquist, Mårten, Kim, Seok Hwan, Bae, Imhyuck, Fokin, Valery V., Sharpless, K. Barry, Chang, Sukbok. Copper-Catalyzed Synthesis of N-Sulfonyl-1,2,3-triazoles: Controlling Selectivity. Angewandte Chemie. international edition, vol.46, no.10, 1730-1733.

  2. Raushel, Jessica, Fokin, Valery V.. Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles. Organic letters, vol.12, no.21, 4952-4955.

  3. Liu, Y., Wang, X., Xu, J., Zhang, Q., Zhao, Y., Hu, Y.. Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates. Tetrahedron, vol.67, no.34, 6294-6299.

  4. Chattopadhyay, Buddhadeb, Gevorgyan, Vladimir. Transition‐Metal‐Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems. Angewandte Chemie. international edition, vol.51, no.4, 862-872.

  5. Davies, Huw M. L., Alford, Joshua S.. Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles. Chemical Society reviews, vol.43, no.15, 5151-5162.

  6. Anbarasan, Pazhamalai, Yadagiri, Dongari, Rajasekar, Shanmugam. Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations­ of 1,2,3-Triazoles and Related Compounds. Synthesis : journal of synthetic organic chemistry, vol.46, no.22, 3004-3023.

  7. Horneff, Tony, Chuprakov, Stepan, Chernyak, Natalia, Gevorgyan, Vladimir, Fokin, Valery V.. Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles. Journal of the American Chemical Society, vol.130, no.45, 14972-14974.

  8. Miura, Tomoya, Yamauchi, Motoshi, Murakami, Masahiro. Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles. Chemical communications : Chem comm, vol.2009, no.12, 1470-1471.

  9. Zibinsky, Mikhail, Fokin, Valery V.. Reactivity of N-(1,2,4-Triazolyl)-Substituted 1,2,3-Triazoles. Organic letters, vol.13, no.18, 4870-4872.

  10. Chattopadhyay, Buddhadeb, Gevorgyan, Vladimir. Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes. Organic letters, vol.13, no.14, 3746-3749.

  11. Spangler, Jillian E., Davies, Huw M. L.. Catalytic Asymmetric Synthesis of Pyrroloindolines via a Rhodium(II)-Catalyzed Annulation of Indoles. Journal of the American Chemical Society, vol.135, no.18, 6802-6805.

  12. Alford, Joshua S., Spangler, Jillian E., Davies, Huw M. L.. Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles. Journal of the American Chemical Society, vol.135, no.32, 11712-11715.

  13. Schultz, Erica E., Sarpong, Richmond. Application of In Situ-Generated Rh-Bound Trimethylenemethane Variants to the Synthesis of 3,4-Fused Pyrroles. Journal of the American Chemical Society, vol.135, no.12, 4696-4699.

  14. Chuprakov, Stepan, Kwok, Sen Wai, Fokin, Valery V.. Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes. Journal of the American Chemical Society, vol.135, no.12, 4652-4655.

  15. Parr, Brendan T., Green, Samantha A., Davies, Huw M. L.. Rhodium-Catalyzed Conversion of Furans to Highly Functionalized Pyrroles. Journal of the American Chemical Society, vol.135, no.12, 4716-4718.

  16. Gulevich, Anton V., Gevorgyan, Vladimir. Versatile Reactivity of Rhodium–Iminocarbenes Derived from N‐Sulfonyl Triazoles. Angewandte Chemie. international edition, vol.52, no.5, 1371-1373.

  17. Zibinsky, Mikhail, Fokin, Valery V.. Sulfonyl‐1,2,3‐Triazoles: Convenient Synthones for Heterocyclic Compounds. Angewandte Chemie. international edition, vol.52, no.5, 1507-1510.

  18. Shi, Yi, Gevorgyan, Vladimir. Intramolecular Transannulation of Alkynyl Triazoles via Alkyne–Carbene Metathesis Step: Access to Fused Pyrroles. Organic letters, vol.15, no.20, 5394-5396.

  19. Miura, Tomoya, Hiraga, Kentaro, Biyajima, Tsuneaki, Nakamuro, Takayuki, Murakami, Masahiro. Regiocontrolled Synthesis of Polysubstituted Pyrroles Starting from Terminal Alkynes, Sulfonyl Azides, and Allenes. Organic letters, vol.15, no.13, 3298-3301.

  20. Liu, Renhe, Zhang, Min, Winston-McPherson, Gabrielle, Tang, Weiping. Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate. Chemical communications : Chem comm, vol.49, no.39, 4376-4378.

  21. Miura, Tomoya, Funakoshi, Yuuta, Murakami, Masahiro. Intramolecular Dearomatizing [3 + 2] Annulation of α-Imino Carbenoids with Aryl Rings Furnishing 3,4-Fused Indole Skeletons. Journal of the American Chemical Society, vol.136, no.6, 2272-2275.

  22. Kwok, Sen Wai, Zhang, Li, Grimster, Neil P., Fokin, Valery V.. Catalytic Asymmetric Transannulation of NH‐1,2,3‐Triazoles with Olefins. Angewandte Chemie. international edition, vol.53, no.13, 3452-3456.

  23. Jung, Da Jung, Jeon, Hyun Ji, Kim, Ju Hyun, Kim, Youngmee, Lee, Sang-gi. DMF as a Source of Oxygen and Aminomethine: Stereoselective 1,2-Insertion of Rhodium(II) Azavinyl Carbenes into the CO Bond of Formamides for the Synthesis of cis-Diamino Enones. Organic letters, vol.16, no.8, 2208-2211.

  24. Tang, Xiang-Ying, Zhang, Yong-Sheng, He, Lv, Wei, Yin, Shi, Min. Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles. Chemical communications : Chem comm, vol.51, no.1, 133-136.

  25. Ko, Young Ok, Jeon, Hyun Ji, Jung, Da Jung, Kim, U Bin, Lee, Sang-gi. Rh(II)/Mg(OtBu)2-Catalyzed Tandem One-Pot Synthesis of 1,4-Oxazepines and 1,4-Oxazines from N-Sulfonyl-1,2,3-triazoles and Glycidols. Organic letters, vol.18, no.24, 6432-6435.

  26. Kim, Cheol-Eui, Park, Sangjune, Eom, Dahan, Seo, Boram, Lee, Phil Ho. Synthesis of Pyrroles from Terminal Alkynes, N-Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1-Sulfonyl-1,2,3-triazoles. Organic letters, vol.16, no.7, 1900-1903.

  27. Kim, Sanghyuck, Mo, Juntae, Kim, Jaeeun, Ryu, Taekyu, Lee, Phil Ho. Aza‐[4+3] and Aza‐[3+2] Annulations for Synthesis of Dihydroazepines and Dihydropyrroles from Alkynes, Sulfonyl Azides, and 1,3‐Dienes. Asian journal of organic chemistry, vol.3, no.9, 926-931.

  28. Kim, Cheol‐Eui, Park, Youngchul, Park, Sangjune, Lee, Phil Ho. Diastereoselective Synthesis of Tetrahydrofurano‐ and Tetrahydropyrano‐dihydropyrroles Containing N,O‐Acetal Moieties via Rhodium‐Catalyzed Transannulation of N‐Sulfonyl‐1,2,3‐triazoles with Oxacycloalkenes. Advanced synthesis & catalysis, vol.357, no.1, 210-220.

  29. Seo, Boram, Jeon, Woo Hyung, Kim, Jaeeun, Kim, Sunghwa, Lee, Phil Ho. Synthesis of Fluorenes via Tandem Copper-Catalyzed [3 + 2] Cycloaddition and Rhodium-Catalyzed Denitrogenative Cyclization in a 5-Exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides in One Pot. Journal of organic chemistry, vol.80, no.2, 722-732.

  30. Ryu, Taekyu, Baek, Yonghyeon, Lee, Phil Ho. Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles. Journal of organic chemistry, vol.80, no.4, 2376-2383.

  31. Lee, Eunsook, Ryu, Taekyu, Shin, Eunji, Son, Jeong-Yu, Choi, Wonseok, Lee, Phil Ho. Synthesis of 2-Bromoimidazoles from Alkynes, N-Sulfonylazides, and Bromocyanides. Organic letters, vol.17, no.10, 2470-2473.

  32. Choi, Wonseok, Kim, Jaeeun, Ryu, Taekyu, Kim, Ki-Bbeum, Lee, Phil Ho. Synthesis of N-Imidoyl and N-Oxoimidoyl Sulfoximines from 1-Alkynes, N-Sulfonyl Azides, and Sulfoximines. Organic letters, vol.17, no.13, 3330-3333.

  33. Kim, Sanghyuck, Kim, Ji Eun, Lee, Jinsub, Lee, Phil Ho. N‐Imidazolylation of Sulfoximines from N‐Cyano Sulfoximines, 1‐Alkynes, and N‐Sulfonyl Azides. Advanced synthesis & catalysis, vol.357, no.16, 3707-3717.

  34. Park, Sangjune, Jeon, Woo Hyung, Yong, Woo-Soon, Lee, Phil Ho. Synthesis of Azulen-1-yl Ketones via Oxidative Cleavage of C–C Multiple Bonds in N-Sulfonyl Enamides and 1-Alkynes under Air and Natural Sunlight. Organic letters, vol.17, no.20, 5060-5063.

  35. Seo, Boram, Jeon, Woo Hyung, Kim, Chul‐Eui, Kim, Sanghyuck, Kim, Sung Hong, Lee, Phil Ho. Sequential Functionalization of the OH and C(sp2)O Bonds of Tropolones by Alkynes and N‐Sulfonyl Azides. Advanced synthesis & catalysis, vol.358, no.7, 1078-1087.

  36. Shin, Seohyun, Son, Jeong-Yu, Choi, Changwook, Kim, Sanghyuck, Lee, Phil Ho. Synthesis of Benzofulvenes through Rhodium-Catalyzed Transannulation of Enynyl Triazoles. Journal of organic chemistry, vol.81, no.23, 11706-11715.

  37. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds Doyle M. P. 1998 

  38. Díaz-Requejo, M. Mar, Pérez, Pedro J.. Coinage Metal Catalyzed C−H Bond Functionalization of Hydrocarbons. Chemical reviews, vol.108, no.8, 3379-3394.

  39. Doyle, Michael P., Duffy, Richard, Ratnikov, Maxim, Zhou, Lei. Catalytic Carbene Insertion into C−H Bonds. Chemical reviews, vol.110, no.2, 704-724.

  40. Davies, Huw M. L., Morton, Daniel. Guiding principles for site selective and stereoselective intermolecular C–H functionalization by donor/acceptor rhodium carbenes. Chemical Society reviews, vol.40, no.4, 1857-1869.

  41. Davies, Huw M. L., Lian, Yajing. The Combined C–H Functionalization/Cope Rearrangement: Discovery and Applications in Organic Synthesis. Accounts of chemical research, vol.45, no.6, 923-935.

  42. Yadagiri, Dongari, Anbarasan, Pazhamalai. Rhodium Catalyzed Direct Arylation of α-Diazoimines. Organic letters, vol.16, no.9, 2510-2513.

  43. Shin, Seohyun, Park, Youngchul, Kim, Cheol-Eui, Son, Jeong-Yu, Lee, Phil Ho. Synthesis of 2-Alkoxyaryl-2-aryl Enamines via Tandem Copper-Catalyzed Cycloaddition and Rhodium-Catalyzed Alkoxyarylation from Alkynes, N-Sulfonyl Azides, and Aryl Ethers. Journal of organic chemistry, vol.80, no.11, 5859-5869.

  44. Park, Sangjune, Yong, Woo-Soon, Kim, Sanghyuck, Lee, Phil Ho. Diastereoselective N-Sulfonylaminoalkenylation of Azulenes from Terminal Alkynes and Azides via N-Sulfonyl-1,2,3-triazoles. Organic letters, vol.16, no.17, 4468-4471.

  45. Danion, Daniel, Arnold, Bernhard, Regitz, Manfred. Pronounced 1,3‐Dipolar Cycloaddition Behavior of an α‐Cyanimino Carbene. Angewandte Chemie. International edition in English, vol.20, no.1, 113-113.

  46. Tietze, L. F., Ferraccioli, R.. Efficient Synthesis of Aza-Heterocycles by a Domino Process using an Inter- and an Intramolecular Heck Reaction. Synlett : accounts and rapid communications in synthetic organic chemistry, vol.1998, no.2, 145-146.

  47. Kubiak, Robert W., Mighion, Jeffrey D., Wilkerson-Hill, Sidney M., Alford, Joshua S., Yoshidomi, Tetsushi, Davies, Huw M. L.. Enantioselective Intermolecular C–H Functionalization of Allylic and Benzylic sp3 C–H Bonds Using N-Sulfonyl-1,2,3-triazoles. Organic letters, vol.18, no.13, 3118-3121.

  48. Grunanger, P., Vita Finzi, P.. Addition reaction of sulfonyl azides on ethoxyacetylene. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.4, no.26, 1839-1840.

  49. Harmon, Robert E., Stanley Jr., Fredrick, Gupta, Swiendra Kumar, Johnson, Jian. N,N-Dialkylamino-1,2,3-triazole-.alpha.-diazoamidine tautomers from substituted benzenesulfonyl azides and ynamines. Journal of organic chemistry, vol.35, no.10, 3444-3448.

  50. McKinney, Michael A., Patel, Parmanand P.. Ring expansions. I. Diazomethane and Tiffeneau-Demjanov ring expansions of norcamphor and dehydronorcamphor. Journal of organic chemistry, vol.38, no.23, 4059-4064.

  51. Himbert, Gerhard, Frank, Dirk, Regit, Manfred. Untersuchungen an Diazoverbindungen und Aziden, XXV 1) Azid‐Additionen an (Silyäthinyl)‐, (Germyläthinyl)‐ und (Stannyläthinyl)amine. Chemische Berichte, vol.109, no.1, 370-394.

  52. Kwok, Sen Wai, Zhang, Li, Grimster, Neil P., Fokin, Valery V.. Catalytic Asymmetric Transannulation of NH‐1,2,3‐Triazoles with Olefins. Angewandte Chemie. international edition, vol.53, no.13, 3452-3456.

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