A simple approach for the synthesis of azocine alkaloids: The total synthesis of megallanesine

Volvoikar, Prajesh S.; Tilve, Santosh G.

doi:10.1016/j.tetlet.2018.05.055

Cited by 6 publications

(3 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[30][31][32][33] It is notwithstanding that the development of selective and practical approach to construct this seemingly simple heterocyclic system is not always trivial. [34][35][36][37][38] In view of the readily accessible characters of starting materials and step economy, direct C-H bond carbonylation of benzylic amines [39][40][41][42] and monoreduction of phthalimide analogues 43,44 have been developed, but nonnegligible limitations are still remained.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

Zhang¹,

Zhao²,

Zhu³

et al. 2021

Preprint

View full text Add to dashboard Cite

<b>Isoindolinone is a class of versatile <i>N</i>-heterocycles embedded in many bioactive molecules and natural products. The invention of new methods to synthesize these heterocyclic compounds with easily accessible chemicals is always attractive. Herein, a conceptually novel approach to access this bicyclic system via isonitrile insertion enabled 1,4-pallaidum shift is described. Compared with conventional isonitrile participated C-H bond activation, both carbon and nitrogen atoms in isonitrile moiety are engaged in new bond formation. Notably, two different isoindolinones can be obtained selectively by switching the bases employed. Mechanistic studies including DFT calculations have shed lights on the reaction mechanism and explained the selectivity led to different products. Moreover, the power of current benzolactamization is further demonstrated by providing concise routes to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine and falipamil.</b>

show abstract

Section: Introductionmentioning

confidence: 99%

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

Zhang¹,

Zhao²,

Zhu³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…Bicyclic N-heterocycles bearing pyrrolidine rings or pyrrolidin-2-one moieties, such as pyrrolizines, indolizines, indolizinones, pyrroloazepines, and pyrroloazocine, are present in bioactive natural products − (Figure ). Methods for the synthesis of these N-heterocycles are of interest in drug discovery and related research. − Whereas various methods for the synthesis of the N-heterocycles have been reported, each can be used only for the synthesis of certain types of N-heterocycles. − Here we report a strategy that allows the synthesis of various pyrrolidinone-fused bicyclic N-heterocycles with different ring sizes (Scheme ).…”

mentioning

confidence: 99%

Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals To Afford Bicyclic N-Heterocycles

2019

View full text Add to dashboard Cite

Acid-catalyzed intramolecular vinylogous Mannich reactions and intramolecular Michael reactions affording pyrrolizinone-fused N-heterocycles from hydroxylactam derivatives bearing enals have been developed. Depending on the substituent on the hydroxylactam, the enal moiety acted either as a nucleophile (i.e., as an enol/enolate) or as an electrophile to react with the N-acyliminium ion or enamide generated from the hydroxylactam moiety, respectively. The reactions were demonstrated in the construction of fused N-heterocycles with 5-to 8-membered rings.B icyclic N-heterocycles bearing pyrrolidine rings or pyrrolidin-2-one moieties, such as pyrrolizines, 1 indolizines, 2 indolizinones, 2 pyrroloazepines, 3 and pyrroloazocine, 3 are present in bioactive natural products 1−3 (Figure 1).

show abstract

“…b-insaturada presente en IV-17, la ruta sintética empleada permitió obtener Magallanesina después de cinco etapas con rendimiento global de 11% 242. …”

unclassified

Síntesis de compuestos aza-bicíclicos por ciclación intramolecular de imidas

Yovanny Quevedo Acosta

View full text Add to dashboard Cite

show abstract

A simple approach for the synthesis of azocine alkaloids: The total synthesis of megallanesine

Cited by 6 publications

References 40 publications

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

Catalytic Benzolactamization Through Isonitrile Insertion Enabled 1,4-Palladium Shift

Intramolecular Mannich and Michael Annulation Reactions of Lactam Derivatives Bearing Enals To Afford Bicyclic N-Heterocycles

Síntesis de compuestos aza-bicíclicos por ciclación intramolecular de imidas

Contact Info

Product

Resources

About