A Novel Iodine‐Promoted Tandem Cyclization: An Efficient Synthesis of Substituted 3,4‐Diiodoheterocyclic Compounds

Ji, Kegong; Zhu, Hongfei; Yang, Fang; Shu, Xing‐Zhong; Zhao, Suoqi; Liu, Xueyuan; Ali, Shaukat; Liang, Yong‐Min

doi:10.1002/chem.201000518

Cited by 58 publications

(27 citation statements)

References 52 publications

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“…Accordingly, to examine the suitability of diverse protecting groups, benzylated 2‐uloside 1 ,, available from d ‐glucose in six steps, was subjected to alkynylation reactions with a set of alkynes including unprotected propargyl alcohol, TIPS‐protected and THP‐protected propargyl alcohol (Scheme ). The addition of free propargyl alcohol was achieved using excessive ethylmagnesium bromide as the base in THF . However, 2a was obtained in only mediocre yields.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Adventures with 2‐C‐Branched Carbohydrates: 4‐C‐Formyl Branched Octoses with Structural Analogy to Bradyrhizose

2019

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The synthesis of three 4‐C‐formyl branched octoses with variable stereoconfiguration at the C‐2 and C‐3 stereogenic centers is described. This class of compounds is of interest due to potential structural analogies to the naturally occurring bradyrhizose monosaccharide. Branched key sugar intermediates of the synthesis are 2‐C‐(1,2,3‐trihydroxyprop‐1‐yl)‐β‐d‐mannosides. A new mild oxidation protocol using known TEMPO/trichloroisocyanuric acid in ethyl acetate/toluene, buffered with 3‐(N‐morpholino)propanesulfonic acid, is described as a valuable reaction for selective primary alcohol oxidation and, hence, the formation of 2‐(spirofuranose)pyranoses. Upon global deprotection these spirofuranoses give complex mixtures of diverse hemiacetal forms of the liberated 4‐C‐formyl octoses. As revealed by detailed NMR studies, the bradyrhizose‐type annulated forms do not represent the major isomers. For each of the target octoses, these potential neighboured acetal‐hemiacetal‐forms (9,7‐pyranose‐1,9‐pyranoses) seem to be unfavorable, and instead remote bis(hemiacetals) are formed (1,5‐pyranose‐9,7‐pyranoses or 1,4‐furanose‐9,7‐pyranoses) as the major species.

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Section: Resultsmentioning

confidence: 99%

Synthetic Adventures with 2‐C‐Branched Carbohydrates: 4‐C‐Formyl Branched Octoses with Structural Analogy to Bradyrhizose

2019

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“…Cooperated with iodine, a relatively stable propargyl carbocation H formed, which could be resonated with allenic carbocation I. [25] By overlapping the p orbital of C C and sp 2 orbital of the allenic carbocation, a vinylic carbocation J was generated. In those solvents without nucleophilicity, the iodide anion attacked the internal carbon atom of allene and afforded a cyclized product 6 a (route a in Scheme 7).…”

Section: Resultsmentioning

confidence: 99%

Four Iodine‐Mediated Electrophilic Cyclizations of Rigid Parallel Triple Bonds Mapped from 1,8‐Dialkynylnaphthalenes

Chen

Lü

Wang

2011

Chemistry A European J

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Four different types of fused arenes, including fluoranthene, indeno[2,1-a]phenalene, (8H)cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene, were efficiently constructed through iodine-mediated electrophilic cyclizations of 1,8-dialkynyl naphthalenes in a single step. Theoretical calculations supported our hypothesis that these reactions had high regioselectivity. Oxidative coupling of the fluoranthene skeleton, followed by aromatization, effectively synthesized perylene derivative 14, which emitted light at 597 nm in dichloromethane with an emission efficiency of 0.81 referred to 5,6,11,12-tetraphenylnaphthacene as a standard.

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“…The required acetylenic 1,4-diols 4 are easily prepared whereas few but highly interesting synthetic application have been described for them in recent years [17] including a remarkable acid-catalyzed domino reaction of highly activated tetraarylbut-2-yne-1,4-diols with 1-naphthol. [18] Scheme 4.…”

Section: Methodsmentioning

confidence: 99%

Brønsted Acid‐Catalyzed Cascade Reactions Involving 1,2‐Indole Migration

Álvarez

Faza

López

et al. 2015

Chemistry A European J

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A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne is here described. DFT calculations support a mechanism consisting in a concerted nucleophilic attack of the indole nucleus with loss of water followed by the 1,2-migration and subsequent Nazarov cyclization. This Brønsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields.

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A Novel Iodine‐Promoted Tandem Cyclization: An Efficient Synthesis of Substituted 3,4‐Diiodoheterocyclic Compounds

Cited by 58 publications

References 52 publications

Synthetic Adventures with 2‐C‐Branched Carbohydrates: 4‐C‐Formyl Branched Octoses with Structural Analogy to Bradyrhizose

Synthetic Adventures with 2‐C‐Branched Carbohydrates: 4‐C‐Formyl Branched Octoses with Structural Analogy to Bradyrhizose

Four Iodine‐Mediated Electrophilic Cyclizations of Rigid Parallel Triple Bonds Mapped from 1,8‐Dialkynylnaphthalenes

Brønsted Acid‐Catalyzed Cascade Reactions Involving 1,2‐Indole Migration

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