One-pot synthesis of polyfunctional pyrazoles: an easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

Shu, Wen‐Ming; Ma, Junrui; Zheng, Kaiyuan; Sun, Hui‐Ying; Wang, Mei; Yang, Yan; Wu, An‐Xin

doi:10.1016/j.tet.2014.10.044

Cited by 30 publications

(23 citation statements)

References 43 publications

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“…imine in dichloromethane in the presence of MgSO 4 . 55 The spectroscopic data of (E)-5c-e, 56 (E)-5h-j, 57 (E)-5f, 58 (E)-5g, 59 (E)-5k, 60 (E)-5l, 61 and (E)-5m 47 are in accordance with reported values.…”

Section: Syn Thesissupporting

confidence: 88%

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

et al. 2016

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A new single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of -diazoketones at high temperature. A number of amides and -lactams were obtained by in situ ketene generation and reaction with amines and imines respectively in good to excellent yields. The preferential formation of trans-configured -lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported and a new web-based molecular viewer, which takes advantage from augmented reality (AR) technology, is also described for a faster interpretation of computed data.

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Section: Syn Thesissupporting

confidence: 88%

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

et al. 2016

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“…Our efforts begun with the preparation of diazodicarbonyl compounds 2a – 2r using a previously reported protocol ,. To optimize the reaction conditions for the synthesis of quinoxaline 3a , the reaction between o ‐phenylenediamine ( 1a ) and ethyl 2‐diazo‐3‐oxobutanoate ( 2a ) in various catalysts and solvents was first examined (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…Newly synthesized diazodicarbonyls ( 2c , 2d , 2e , 2g , 2h , 2i , 2m , 2q and 2r ) have been completely characterized by NMR, FT‐IR and HR‐MS whereas known diazodicarbonyls ( 2a , 2b , 2f , 2j , 2l , 2n and 2o ) and 2k were characterized by NMR only. Diazoketone 2p was prepared by a known method (see the Supporting Information for details).…”

Section: Methodsmentioning

confidence: 99%

Iron‐Catalyzed Annulation of 1,2‐Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water

2016

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An ovela nd facile iron-catalyzed tandem annulation of o-phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. Thek ey strategyi ncludest he one-pot domino N À Hi nsertion, cyclization, and oxidation reactions.T his protocol offersasafe andm ild synthetic approach to access av arietyo fq uinoxaline derivatives in high yields. This methodology also allowst he formation of biologically interesting pyrazines and benzoquinoxalines.

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“…To prepare for the crucial insertion reaction, 11 was acylated under Friedel–Crafts conditions to afford the methyl ketone 12 (67 %; Scheme ), which was then subjected to Riley oxidation conditions to afford the ketoaldehyde 13 as a mixture with (presumably) its hydrate (not shown). Reaction of this mixture with tosyl hydrazide in the presence of Cs 2 CO 3 afforded the diazoketone 14 (86 %, 2 steps), which set the stage for the key carbene insertion reaction. Reaction of 14 with 1 mol % Rh 2 (OAc) 4 at 40 °C in dichloromethane smoothly afforded the indanone derivative 15 (54 %).…”

Section: Methodsmentioning

confidence: 99%

Contractive Annulation: A Strategy for the Synthesis of Small, Strained Cyclophanes and Its Application in the Synthesis of [2](6,1)Naphthaleno[1]paracyclophane

et al. 2019

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One-pot synthesis of polyfunctional pyrazoles: an easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

Cited by 30 publications

References 43 publications

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

Iron‐Catalyzed Annulation of 1,2‐Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water

Contractive Annulation: A Strategy for the Synthesis of Small, Strained Cyclophanes and Its Application in the Synthesis of [2](6,1)Naphthaleno[1]paracyclophane

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