Copper (triazole-5-yl)methanamine complexes onto MCM-41: the synthesis of pyridine-containing pseudopeptides through the 6-endo-dig cyclization of 1,5-enynes

Neda Akbarikalani; Kamran Amiri; Ahmed Al-Harrasi; Saeed Balalaie

doi:10.1039/c9ra10885h

Copper (triazole-5-yl)methanamine complexes onto MCM-41: the synthesis of pyridine-containing pseudopeptides through the 6-endo-dig cyclization of 1,5-enynes

RSC Advances ◽

10.1039/c9ra10885h ◽

2020 ◽

Vol 10 (18) ◽

pp. 10577-10583

Author(s):

Neda Akbarikalani ◽

Kamran Amiri ◽

Ahmed Al-Harrasi ◽

Saeed Balalaie

Keyword(s):

Nucleophilic Addition ◽

Cyclization Reaction ◽

Enyne Cyclization ◽

Mcm 41

A sequential Ugi/nucleophilic addition/1,5-enyne cyclization reaction was used for the synthesis of pseudopeptides containing pyridine skeletons in the presence of Cu@TZMA@MCM-41.

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Transition Metal-Catalyzed Intramolecular Enyne Cyclization Reaction

Current Organic Chemistry ◽

10.2174/138527206778018203 ◽

2006 ◽

Vol 10 (12) ◽

pp. 1457-1478 ◽

Cited By ~ 57

Author(s):

Z. Zhang ◽

G. Zhu ◽

X. Tong ◽

F. Wang ◽

X. Xie ◽

...

Keyword(s):

Transition Metal ◽

Cyclization Reaction ◽

Enyne Cyclization ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Cobalt-Catalyzed Cyclization of 2-Bromobenzamides with Carbodiimides: A New Route for the Synthesis of 3-(Imino)isoindolin-1-ones

Molecules ◽

10.3390/molecules26237212 ◽

2021 ◽

Vol 26 (23) ◽

pp. 7212

Author(s):

Hasil Aman ◽

Yu-Chiao Huang ◽

Yu-Hao Liu ◽

Yu-Lin Tsai ◽

Min Kim ◽

...

Keyword(s):

Reaction Mechanism ◽

Catalytic Reaction ◽

Nucleophilic Addition ◽

Cyclization Reaction ◽

Synthetic Pathway

A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.

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One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes

Synlett ◽

10.1055/s-0037-1611760 ◽

2019 ◽

Vol 30 (07) ◽

pp. 857-859 ◽

Cited By ~ 2

Author(s):

Fen Tan ◽

Zheng-Zheng Meng ◽

Xiao-Qin Xiong ◽

Guo-Ping Zeng ◽

Ming-Wu Ding

Keyword(s):

Nucleophilic Addition ◽

Cyclization Reaction ◽

Regioselective Synthesis ◽

One Pot ◽

Tosyl Chloride ◽

Aryl Isocyanates ◽

Wittig Reactions

A new, one-pot, regioselective preparation of 2,5,6,7-tetrahydroimidazo[1,2-a]imidazol-3-ones by a sequential aza-Wittig/nucleophilic addition/cyclization reaction was developed. The aza-Wittig reactions of ethyl (2Z)-3-aryl-2-[(triphenylphosphoranylidene)amino] acrylates with aryl isocyanates produced carbodiimide intermediates that were then treated sequentially with 2-aminoethanol and tosyl chloride/triethylamine to give the corresponding (2Z)-2-[(substituted)benzylidene]-2,5,6,7-tetrahydro-3H-imidazo[1,2-a]imidazol-3-ones in good overall yields and with high regioselectivity.

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Tandem Nucleophilic Addition/Cyclization Reaction in the Synthesis of Ketimine-Type Iminosugars

The Journal of Organic Chemistry ◽

10.1021/jo702616x ◽

2008 ◽

Vol 73 (9) ◽

pp. 3612-3615 ◽

Cited By ~ 12

Author(s):

Jean-Bernard Behr ◽

Adel Kalla ◽

Dominique Harakat ◽

Richard Plantier-Royon

Keyword(s):

Nucleophilic Addition ◽

Cyclization Reaction

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Phase-transfer-catalyzed cyclization reaction of nucleophilic addition to electron-deficient 1,3-conjugated enynes for the synthesis of functionalized 4H-pyrans

Organic & Biomolecular Chemistry ◽

10.1039/c0ob01255f ◽

2011 ◽

Vol 9 (9) ◽

pp. 3375 ◽

Cited By ~ 9

Author(s):

Jie Hu ◽

Lei Liu ◽

Shangdong Yang ◽

Yong-Min Liang

Keyword(s):

Nucleophilic Addition ◽

Phase Transfer ◽

Cyclization Reaction ◽

Conjugated Enynes

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ChemInform Abstract: Phase-Transfer-Catalyzed Cyclization Reaction of Nucleophilic Addition to Electron-Deficient 1,3-Conjugated Enynes for the Synthesis of Functionalized 4H-Pyrans.

ChemInform ◽

10.1002/chin.201136136 ◽

2011 ◽

Vol 42 (36) ◽

pp. no-no

Author(s):

Jie Hu ◽

Lei Liu ◽

Shangdong Yang ◽

Yong-Min Liang

Keyword(s):

Nucleophilic Addition ◽

Phase Transfer ◽

Cyclization Reaction ◽

Conjugated Enynes

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Transition Metal Catalyzed Intramolecular Enyne Cyclization Reaction

ChemInform ◽

10.1002/chin.200644226 ◽

2006 ◽

Vol 37 (44) ◽

Author(s):

Z. Zhang ◽

G. Zhu ◽

X. Tong ◽

F. Wang ◽

X. Xie ◽

...

Keyword(s):

Transition Metal ◽

Cyclization Reaction ◽

Enyne Cyclization ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction

Synthesis ◽

10.1055/s-0037-1612279 ◽

2019 ◽

Vol 51 (11) ◽

pp. 2402-2408

Author(s):

Zhi-Rong Guan ◽

Shuai Liu ◽

Zi-Ming Liu ◽

Ming-Wu Ding

Keyword(s):

Nucleophilic Addition ◽

Wittig Reaction ◽

Cyclization Reaction ◽

Primary Amines ◽

Efficient Synthesis ◽

One Pot ◽

Sodium Alkoxide

A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.

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