Use of chloroalkenylamines for the synthesis of 1-azabicyclo[3.3.0]octane and 1-azabicyclo[4.3.0]nonane derivatives

Lochead, Alistair W.; Proctor, G. R.; Caton, M.P.L.

doi:10.1039/p19840002477

Cited by 23 publications

(18 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Vilsmeier–Haack cyclization is endo – exo according to Ben-Ishai nomenclature for sp 2 nucleophiles reacting with sp 2 electrophiles . Hence, the electrophilic triflyliminium ion resulting from amide activation is endocyclic with respect to the ring in formation, and the nucleophile is exocyclic for all substrates of Table , except for 28f , which presents an endo – endo cyclization mode .…”

Section: Results and Discussionmentioning

confidence: 99%

Sequential One-Pot Vilsmeier–Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

2020

View full text Add to dashboard Cite

The development of new one-pot sequential cyclizations involving a Vilsmeier–Haack reaction followed by an organocatalyzed Mannich reaction is reported. This synthetic strategy gives access to functionalized indolizidines and quinolizidines in one operation from readily synthesized precursors. Yields and diastereoselectivities are good to excellent when formamides are used to trigger the key step, bearing either an electron-rich aryl or a pyrrole as the nucleophilic partner in the first cyclization.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Sequential One-Pot Vilsmeier–Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

2020

View full text Add to dashboard Cite

show abstract

“…Proctor et al reported a two-step synthesis of (�)-crispine A (�)-1 in 1984 starting from L-proline (Scheme 4). [32] The reaction of β-aryl ethyl chloride 11 with L-proline 12 in the presence of potassium carbonate in methanol afforded N-alkylated adduct 13. The reaction of this N-alkyl proline 13 with phosphoryl chloride at elevated temperature facilitated Bischler-Napieralski cyclization via iminium ion intermediate 14 to obtain (�)crispine A (�)-1 with an overall yield of 14 %.…”

Section: Reactions Involving Bischler-napieralski Cyclizationmentioning

confidence: 99%

Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

et al. 2021

View full text Add to dashboard Cite

As a naturally occurring small-molecule, various optical isomers of chiral pyrrolo[2,1-a]isoquinoline alkaloid crispine A represent a potential class of chiral molecules in contemporary organic chemistry, and possess diverse biological activities. The range of pharmacological activities include antidepressant, antiplatelet, antileukemic, and anticancer activities. This review provides an overview of the literature on the strategies, employed in the synthesis of crispine A in their racemic and enantiopure forms via Bischler-Napieralski cyclization, Pictet-Spengler cyclization, N-Alkylation/Acylation-cyclization, Oxidative cyclization, and Asymmetric hydrogenation in the period of 1931-2021. This study accentuates the need for the developing more effective synthesis, and search for involved biological applications for the pyrroloisoquinoline class of natural product. Attention has been drawn towards the use of relatively less documented but easily accessible naturally occurring diastereomeric scaffolds namely, garcinia and hibiscus acids. These lactones obtained from (+)and (À )-2-hydroxycitric acids bearing chemically amenable functional groups are investigated as an ideal choice for the enantiopure synthesis of the (À )-(R)-and (+)-(S)-Crispine A structural frame work.

show abstract

“…Compound 7ga was prepared from 1-benzylproline (2a) and 1,3-dimethylbarbituric acid (6g) by General procedures A and C. The product was purified by flash column chromatography (CHCl 3 / MeOH = 99:1 to 98:2) to give 7ga (yellow oil, 0.0472 g, 0.15 mmol, 30%, R f = 0.47 (CH 2 Cl 2 /MeOH = 9:1)). 1 (10). To a mixture of 2-(1-benzylpyrrolidin-2-yl)-1-(3,4-dimethoxyphenyl)ethanone (5ha, 0.1185 g, 0.3491 mmol, 1 equiv) in methanol (0.70 mL) was added sodium borohydride (0.02641 g, 0.6982 mmol, 2 equiv) and cerium(III) chloride heptahydrate (0.2601 g, 0.6982 mmol, 2 equiv).…”

Section: ■ Conclusionmentioning

confidence: 99%

Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

et al. 2015

View full text Add to dashboard Cite

2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

show abstract

Use of chloroalkenylamines for the synthesis of 1-azabicyclo[3.3.0]octane and 1-azabicyclo[4.3.0]nonane derivatives

Cited by 23 publications

References 13 publications

Sequential One-Pot Vilsmeier–Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

Sequential One-Pot Vilsmeier–Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids

Contact Info

Product

Resources

About