Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine

Silva, Siguara Bastos Lemos; Torre, Adriana Della; Carvalho, João Ernesto de; Ruiz, Ana Lúcia Tasca Góis; Silva, Luiz F.

doi:10.3390/molecules20011475

Cited by 22 publications

(14 citation statements)

References 70 publications

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“…Finally, the oxidation of tetrahydroquinoline 31 was examined. Following the evaluation of various reaction conditions [32][33][34], the best outcome was obtained upon treatment of 31 with KMnO 4 and MgSO 4 in an acetone-H 2 O solvent system [35]. Employing these conditions, trigonoine B (1) was obtained in 43% yield.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

Nishiyama¹,

Hamada²,

Ishii³

et al. 2021

Beilstein J. Org. Chem.

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The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoine B (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoine B (1) in 9.2% overall yield. The described route could be employed for the preparation of various N-substituted 4-aminopyrroloquinolines with various biological activities.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

Nishiyama¹,

Hamada²,

Ishii³

et al. 2021

Beilstein J. Org. Chem.

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“…Adapted from ref. [60] The cascade sequence involves HIBT vinyl activation, ring expansion/oxidation, elimination and further methanol addition to afford products 155, 157 and 158. HIBT promotes ring expansion through forming carbocation 153.…”

Section: Ring Expansions Of Vinylcycloalkanolsmentioning

confidence: 99%

“…This is followed by methanol addition under reaction conditions to produce 158 via path B (Scheme 34). [ 60 ]…”

Section: Ring Expansionsmentioning

confidence: 99%

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

et al. 2020

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This minireview focuses on recent advances in the synthesis of seven-membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring-closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium-type species. Also discussed [a] Prof.

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“…Another method enables conversion of silyl ethers 62 into the corresponding cycloheptanones 63 (Scheme 19) [16,17]. In this case, a tandem oxidative ring expansion and addition promoted by HTIB (PhI(OH)OTs) occurs through the formation of a cycloheptenone intermediate.…”

Section: Ring Expansions and Contractionsmentioning

confidence: 99%

Rearrangements Induced by Hypervalent Iodine

Maertens

Canesi

2015

Topics in Current Chemistry

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This chapter describes advances in hypervalent iodine(III)-induced rearrangements reported between 2004 and 2015, beginning with Hofmann-type rearrangements and aliphatic aryl transpositions. In both reactions the iodine(III) reagent may be off-the-shelf or catalytically generated in situ. A number of stereoselective transformations are discussed, followed by transpositions triggered through phenol dearomatization, including Wagner-Meerwein-type rearrangements, Prins-pinacol transpositions, and a tandem polycylization-pinacol process. Other rearrangements such as an iodonio-Claisen rearrangement, an ipso-rearrangement, and rearrangements performed using iodine(V) are also described.

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Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine

Cited by 22 publications

References 70 publications

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

Rearrangements Induced by Hypervalent Iodine

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