129518-37-2Relevant academic research and scientific papers
One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds
Song, Qiao,Liu, Yan,Cai, Linlin,Cao, Xinyu,Qian, Shan,Wang, Zhouyu
, p. 1713 - 1716 (2021/03/08)
Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.
Synthetic method of tetrahydroisoquino ring compound and tetrahydro-beta-carbo ring compound
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Paragraph 0047-0052; 0203; 0205-0207, (2020/12/09)
The invention provides a synthetic method of a tetrahydroisoquino ring compound and a tetrahydro-beta-carbo ring compound, and belongs to the technical field of synthesis. According to the method forsynthesizing the tetrahydroisoquino and the tetrahydro-b
TMSOTf mediated '5/6-: Endo-dig ' reductive hydroamination for the stereoselective synthesis of pyrrolidine and piperidine derivatives
Gharpure, Santosh J.,Vishwakarma, Dharmendra S.,Patel, Raj K.
, p. 6858 - 6861 (2019/06/18)
A TMSOTf mediated 5/6-endo-dig reductive hydroamination cascade on internal alkynylamines gave expedient, stereoselective access to pyrrolidine and piperidine derivatives. We also demonstrate that a protecting group on nitrogen has a profound effect on the reactivity as well as diastereoselectivity of the reductive hydroamination cascade.
Diastereoselective allylation of 3,4-dihydro-4-phenylisoquinoline. Convenient methods for the preparation of cis- and trans-1-allyl-4-phenyl-1,2,3, 4-tetrahydroisoquinoline#
Taketoshi, Ayako,Hosoda, Naoya,Yamaguchi, Yoshitaka,Asami, Masatoshi
experimental part, p. 2418 - 2424 (2009/09/25)
Diastereoselective allylation of 3,4-dihydro-4-phenylisoquinoline by several allylating reagents was examined. Reactions using allyltin or allylsilane in the presence of alkyl chloroformate and a catalytic amount of trimethylsilyl triflate gave trans-1-allyl-4-phenyl-1,2,3,4- tetrahydroisoquinoline with moderate diastereoselectivity. In contrast, cis-1-allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline was obtained predominantly in the reactions using allyllithium, triallylborane, allylzinc bromide, and diallylzinc. cis-1-Allyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline was transformed to (6S*,10bR*)-hexahydro-6-phenylpyrrolo[2,1-a]isoquinoline, a potential antidepressant agent, in five steps.
Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants
Sorgi, Kirk L.,Maryanoff, Cynthia A.,McComsey, David F.,Graden, David W.,Maryanoff, Bruce E.
, p. 3567 - 3579 (2007/10/02)
Reductive deoxygenation of 5a, 5b, 7a, or 7b with borane-THF in trifluoroacetic acid yielded a product mixture (6a/6b or 4a/4b) highly biased (90-95%) in favor of the trans diastereomer (6b or 4b). The mechanism of this process was probed by NMR spectrosc
A CONVENIENT ASYMMETRIC SYNTHESIS OF PYRROLOISOQUINOLINES
Meyers, A. I.,Guiles, Joseph
, p. 2813 - 2816 (2007/10/02)
A four-step synthesis of optically pure 6α-phenyl pyrroloisoquinolines from chiral formamidines has been accomplished.
HIGHLY STEREOCONTROLLED PROTON TRANSFER IN AN ENAMMONIUM-IMINIUM REARRANGEMENT. MECHANISM OF THE STEREOSELECTIVE DEOXYGENATION OF 6-ARYL-6-HYDROXY-1,2,3,5,6,10b-HEXAHYDROPYRROLOISOQUINOLINES WITH BORANE-THF IN TRIFLUOROACETIC ACID.
Maryanoff, Bruce E.,McComsey, David F.,Mutter, Martin S.,Sorgi, Kirk L.,Maryanoff, Cynthia A.
, p. 5073 - 5076 (2007/10/02)
Either diastereomer of 2 or 10 is deoxygenated with BH3-THF/CF3CO2H to give mainly the trans product, 3b or 11b.The process involes a key enammonium-iminium rearrangement in which there is almost exclusive proton delivery from a single face.
Hexahydropyrrolo[2,1-a]isoquinoline derivatives and antidepressant use thereof
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, (2008/06/13)
Novel compounds are disclosed, which are derivatives of 1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]-isoquinolines, represented by general formula (I): STR1 as well as pharmaceutical compositions and methods for the treatment of depression in warm-blooded animals, e.g., man. Novel intermediates are also part of the invention.
Stereochemistry of Intramolecular Amidoalkylation Reactions in the Synthesis of Polycyclic Isoquinoline Derivatives
Maryanoff, Bruce E.,McComsey, David F.,Duhl-Emswiler, Barbara A.
, p. 5062 - 5074 (2007/10/02)
N-Acyliminium cyclizations onto benzenoid rings to give tetrahydroisoquinoline ring systems were studied.Particular attention was paid to the stereochemical effect of substituents present on the isoquinoline ring.High stereoselectivity (> 90 percent) was
