Copper-Mediated Cascade C–H/N–H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids

Zhang, Tingyu; Liu, Chang; Chen, Chao; Liu, Jianxin; Xiang, Heng-Ye; Jiang, Wei; Ding, Tong‐Mei; Zhang, Shuyu

doi:10.1021/acs.orglett.7b03580

Cited by 76 publications

(33 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“… [69] Miura et al . found that removal of MQ from benzolactams 285/286 was possible in moderate yields, but only when more forcing conditions were used (BBr 3 followed by a hypervalent iodine oxidant) [73, 175, 176] . Interestingly, Daugulis et al .…”

Section: Oxidative Cleavage Of the Amide Bondmentioning

confidence: 99%

A Guide to Directing Group Removal: 8‐Aminoquinoline

Fitzgerald

O’Duill

2021

Chemistry A European J

View full text Add to dashboard Cite

The use of directing groups allows high levels of selectivity to be achieved in transition metal‐catalyzed transformations. Efficient removal of these auxiliaries after successful functionalization, however, can be very challenging. This review provides a critical overview of strategies used for removal of Daugulis’ 8‐aminoquinoline (2005–2020), one of the most widely used N,N‐bidentate directing groups. The limitations of these strategies are discussed and alternative approaches are suggested for challenging substrates. Our aim is to provide a comprehensive end‐users’ guide for chemists in academia and industry who want to harness the synthetic power of directing groups—and be able to remove them from their final products.

show abstract

Section: Oxidative Cleavage Of the Amide Bondmentioning

confidence: 99%

A Guide to Directing Group Removal: 8‐Aminoquinoline

Fitzgerald

O’Duill

2021

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The 3d transition‐metals like copper has grave attention toward C−H/NH annulations for the synthesis of alkaloids and biologically active molecules [62] . Similarly in 2018, Zhang and his group [63] reported C−H/N−H annulations mediated by copper to construct tetracyclic indoloquinolines (tetrahydro‐β‐carbolinones, 21 ) using CsF and TBAI in the presence of molecular oxygen from indolo‐2‐carboxamides ( 19 ). The electron‐donating and withdrawing group containing indole derivatives were participated in the reaction with significant yield.…”

Section: Synthesis Of β‐Carbolinesmentioning

confidence: 99%

Application of Transition Metal‐Catalyzed C−H Activation Strategies in the Synthesis and Functionalization of β‐Carbolines

2021

View full text Add to dashboard Cite

β-Carboline and its derivatives are well-known for their biological and pharmacological properties and are considered as an important source of drug or drug leads. The traditional methods employed for the construction of βcarbolines present certain limitations surfacing requirements for a better approach. The catalytic CÀ H activation strategy offers an attractive route owing to step-and atom-economy. The transition metal-catalyzed CÀ H activation has not just been employed for the synthesis of β-carboline scaffold but also has paved the way for functionalization, scrutinizing the intrinsic directing property of β-carbolines. This review focuses on exploring the efficiency of CÀ H activation in fabricating and functionalizing β-carbolines, including the overview of substrate scope, regioselectivity and synthesis of some of the related natural products.

show abstract

“…The Zhang group developed several copper-mediated syntheses of natural products and in 2018 reported a selective cascade C-H/N-H annulation strategy toward the tetracyclic core of isocryptolepine, thus providing a new formal total synthesis of the natural product. 156 The bond forming approach is mediated by a 8-aminoquinoline N,Nbidentate directing group 157 and involves a reaction with a benzyne derivative under mild conditions.…”

Section: D Syntheses From Indolesmentioning

confidence: 99%