- Electrochemical synthesis of isobenzofuran-1-imines using oxidative halocyclization ofo-alkynylbenzamides
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Electrochemical oxidative 5-exo-dig-oxo-halocyclization ofo-alkynylbenzamides was achieved using readily available NaX (X = Cl, Br and I) salts under mild reaction conditions. The use of a cheap and highly stable sodium halide as a halide ion source is im
- Anandhan, Ramasamy,Bhagavathiachari, Muthuraaman,Bhargava Reddy, Mandapati,Peri, Rajagopal
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supporting information
p. 6792 - 6796
(2021/08/20)
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- Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones
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Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
- Mehta, Saurabh,Brahmchari, Dhirendra
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p. 5492 - 5503
(2019/05/10)
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- Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides
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A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I2/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C=C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.
- Brahmchari, Dhirendra,Verma, Akhilesh K.,Mehta, Saurabh
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supporting information
p. 3339 - 3347
(2018/03/23)
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- Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins
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Synthesis of isocoumarins and related compounds via triflic acid promoted hydrolysis/cyclization sequence of 2-(alkynyl)benzamides under microwave condition was achieved. The substrate scope of the reaction was broad to include not only aromatic but also
- Praveen, Chandrasekaran,Dheenkumar,Perumal
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- Synthesis of 1-aminoisoquinolines by gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate
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A facile synthetic route toward pharmaceutically interesting 1-aminoisoquinoline derivatives by gold(III)-mediated domino reactions is described. This synthetic protocol starts from readily available 2-alkynylbenzamides and ammonium acetate and takes plac
- Long, Yuhua,She, Zhigang,Liu, Xiaochen,Chen, Yu
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p. 2579 - 2588
(2013/04/24)
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- Photo-induced sonogashira C-C coupling reaction catalyzed by simple copper(I) chloride salt at room temperature
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The conventional thermal Sonogashira C-C coupling reaction requires the use of a palladium catalyst and a large amount of ligands. Although there were a few reports describing the use of inexpensive metal catalysts, such as, copper (Cu), iron (Fe), and nickel (Ni), for replacement of palladium (Pd) in the Sonogashira reactions, it was later questioned that the observed effects were due to ppb levels contamination of Pd present in the reagents used in the reactions. Herein, we report that simple copper(I) chloride (CuCl) salt, in the absence of Pd and ligands, can catalyze the Sonogashira reaction with high yields (80-99%) under blue LED light irradiation at room temperature. Control experiments show that no cross-coupling product was formed, when palladium(II) chloride (PdCl2) was used to replace CuCl as a catalyst. A series of electron-rich and electron-poor substituted aryl halides (bromides and iodides) as well as aryl- and alkylacetylenes are examined and the reaction mechanism is discussed.
- Sagadevan, Arunachalam,Hwang, Kuo Chu
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supporting information
p. 3421 - 3427
(2013/02/22)
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- Regio- and stereoselective synthesis of cyclic imidates via electrophilic cyclization of 2-(1-alkynyl)benzamides. A correction
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The electrophilic cyclization of 2-(1-alkynyl)benzamides affords high yields of cyclic imidates, instead of the previously reported isoindolin-1-ones, where cyclization proceeds on the oxygen of the carbonyl group rather than the nitrogen of the amide fun
- Mehta, Saurabh,Yao, Tuanli,Larock, Richard C.
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supporting information
p. 10938 - 10944
(2013/02/22)
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- Copper(II)chloride-mediated cyclization reaction of N-alkoxy- orthoalkynylbenzamides
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A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.
- Jithunsa, Manita,Ueda, Masafumi,Miyata, Okiko
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supporting information; experimental part
p. 518 - 521
(2011/04/16)
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- Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: Synthesis of 1-alkoxyisoquinolines and isoquinolones
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A facile synthesis of a series of 1-alkoxyisoquinolines and (2H)-isoquinolones by an intramolecular 6-endo-dig cyclization of ortho-alkynylbenzonitriles in the presence of a catalytic amount of hydrido(dimethylphosphinous acid-κP)[hydrogen bis(dimethylphosphinito- κP)]platinum(II) in various alcohols at 65-90 °C is described for the first time.
- Li, Jim,Chen, Lijing,Chin, Elbert,Lui, Alfred S.,Zecic, Hasim
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experimental part
p. 6422 - 6425
(2010/12/25)
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- Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization
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(Chemical Equation Presented) A variety of substituted isoindolin-1-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICl, I2, and NBS. In a few cases, subs
- Yao, Tuanli,Larock, Richard C.
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p. 1432 - 1437
(2007/10/03)
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- Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones
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A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.
- Kundu, Nitya G.,Khan, M. Wahab
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p. 4777 - 4792
(2007/10/03)
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- A direct anionic cyclization of 2-alkynylbenzonitrile to 3- substituted-1(2H)-isoquinolones and 3-benzylideneisoindol-2ones initiated by methoxide addition
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Treatment of 2-(2-alkylethynyl)benzonitrile with sodium methoxide in refluxing methanol for 12 h gave 3-alkyl-1(2H)- isoquinolone in modest yield. Under the same reaction conditions, methanolysis of 2-(2-arylethynyl)benzonitrile lead to the formation of 3
- Wu, Ming-Jung,Chang, Li-Juan,Wei, Li-Mei,Lin, Chi-Fong
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p. 13193 - 13200
(2007/10/03)
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- A highly regio and stereoselective synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones via palladium catalyzed annulation of terminal alkynes
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o-Iodobenzamide or its N-substituted derivatives 4-10 and terminal alkynes 11-17 reacted in DMF in the presence of bis(triphenylphosphine)palladium(II)chloride, cuprous iodide and triethylamine leading to (Z)-3- arylidene isoindolin-1-ones (22, 24, 27 and 28) or o-alkynyl N-substituted benzamides (I). The latter could be cyclised with sodium in ethanol in a completely regio and stereoselective manner to (Z)-3-aryl(alkyl)idene isoindolin-1-ones 18-35.
- Khan, M. Wahab,Kundu, Nitya G.
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p. 1435 - 1437
(2007/10/03)
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- Condensed heteroaromatic ring systems. XXIV. Palladium-catalyzed cyclization of 2-substituted phenylacetylenes in the presence of carbon monoxide
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The palladium-catalyzed reaction of 2-alkynylanilines and 2-alkynylphenols in the presence of carbon monoxide and methanol under basic conditions gave the sequential cyclization/carbonylation products, methyl 2-substituted indole and benzo[b]furan-3-carbo
- Kondo, Yoshinori,Shiga, Futoshi,Murata, Naoko,Sakamoto, Takao,Yamanaka, Hiroshi
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p. 11803 - 11812
(2007/10/02)
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- CYCLIZATION OF VICINAL ACETYLENIC DERIVATIVES OF PYRAZOLECARBONAMIDES AND BENZAMIDES
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Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or five-membered lactam ring.The formation of γ-lactam (from o-phenylethynylbenzamide) has been noted for t
- Vasilevskii, S. F.,Shvartsberg, M. S.
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p. 1901 - 1905
(2007/10/02)
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