An expedient approach for the regio- and stereoselective synthesis of novel spiroindolizidines via [3+2] cycloaddition

Alimohammadi, Kamal; Sarrafi, Yaghoub; Rajabpour, Bahareh

doi:10.1016/j.crci.2013.06.003

Cited by 11 publications

(6 citation statements)

References 48 publications

(8 reference statements)

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“…reported a regio‐ and stereoselective reaction between THIQ 3 , ninhydrin 127 /isatins 130 and trans ‐ β ‐nitrostyrenes 126 in refluxng ethanol (Scheme 26). [42] Under this condition, a wide range of spiroindolizidines 129 and 131 were obtained in good to high yields (82–95%). As the authors discussed, when isatins 130 were used as substrate, the corresponding spiroindolizidines 131 were obtained in good to high yields (82–92%) as major products; whereas the reaction of ninhydrine 127 as substrate with THIQ 3 and β ‐nitrostyrenes 126 produced the other spiroindolizidines derivatives 129 in good to high yields (82–95%) as the sole product.…”

Section: C1‐functionalization With Annulationmentioning

confidence: 92%

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

et al. 2021

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1,2,3,4‐tetrahydroisoquinoline (THIQ) and its derivatives possess a widespread biochemical, pharmaceutical and biological properties and they are the key building blocks in the structure of drugs and natural alkaloids. Accordingly, construction of multi‐substituted and polycyclic THIQs through functionalization of THIQs at different positions especially at C1‐position have come to the center of attraction in recent studies. In this review, we've focused on the classification of C1‐functionalization of THIQs in the research articles from 2013 on, including a brief description of the reaction mechanisms for the synthesis of multi‐substituted and polycyclic THIQs based on the type of substituents at the 1‐position of the THIQ moiety. From this point of view, the main categories are C1‐Functionalization and C1‐Functionalization with annulation.

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Section: C1‐functionalization With Annulationmentioning

confidence: 92%

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

et al. 2021

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“…The reaction was performed by stirring an equimolar amount of starting materials in ethanol at reux temperature for 2-3 h (Scheme 26). 41 3-Nitrochromenes 79 were used as 2p components in the 1,3dipolar cycloaddition reactions with various azomethine ylides 80 to achieve polysubstituted benzopyrano[3,4-c]-pyrrolidines 81 in the presence of AgOAc/Et 3 N as catalyst (Scheme 27). 42 It is notable that the one-pot three-component reactions of 3nitrochromenes, sarcosine or N-benzylglycine and aldehydes also afforded the corresponding cycloaddition products in reuxing toluene in high to excellent yields.…”

Section: Synthesis Of Five-membered Heterocyclesmentioning

confidence: 99%

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

2014

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The applications of nitroalkenes in the synthesis of three-to five-membered O, N and S-heterocycles, including natural products are investigated in this review. These heterocyclic compounds were synthesized from nitroalkenes with a variety of substituents at the a and b-positions and those that were part of common and medium rings via a wide variety of reactions such as Michael addition reactions, epoxidation, [3 + 2] cycloaddition and many cascade/domino/tandem reactions. In addition, the potential of nitroalkenes to take part in multi-component and cascade reactions, particularly, in diastereo-and enantioselective versions is reviewed. The high reactivity of nitroalkenes and their potential to coordinate with the metal catalysts as well as organocatalysts signify them as efficient precursors in synthetic organic chemistry. Also, the flexibility of the nitro group in functional group manipulations has expanded the scope of the nitro group, in general, and nitroalkenes, in particular, in organic synthesis.

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“…73 The reaction afforded a series of novel spiroindolizidines 82 as major products in a similar regio-and stereocontrolled manner. © ARKAT-USA, Inc. …”

Section: Scheme 29mentioning

confidence: 99%

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Ziarani¹,

Moradi²,

Lashgari³

2015

Arkivoc

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Isatin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of multi-component reactions that include isatin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of isatin as starting material in the synthesis of various organic compounds and drugs during the period from 2012 to 2015.

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An expedient approach for the regio- and stereoselective synthesis of novel spiroindolizidines via [3+2] cycloaddition

Cited by 11 publications

References 48 publications

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

Part I: Nitroalkenes in the synthesis of heterocyclic compounds

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

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