- Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
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Reactions of o-alkynylisocyanobenzenes with a variety of alkanethiols (Alk-SH) provide the corresponding bis-thiolated indole derivatives. The advantages of the reaction include metal-free, room-temperature, mild reaction conditions and broad functional group compatibility. The reaction proceeds via nucleophilic addition of an alkanethiol to an isonitrile moiety, 5-exo cyclization, followed by nucleophilic addition of an alkanethiol to a 3-alkylidene indole intermediate. Density functional calculations on the electronic structures and relative free energies of 5-exo and 6-endo cyclization pathways support that the 5-exo cyclization is preferable.
- La-Ongthong, Kannika,Naweephattana, Phiphop,Khaikate, Onnicha,Surawatanawong, Panida,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Kuhakarn, Chutima
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p. 6338 - 6351
(2020/07/21)
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- Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines
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An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.
- Khaikate, Onnicha,Soorukram, Darunee,Leowanawat, Pawaret,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
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p. 7050 - 7057
(2019/11/11)
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- Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
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A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
- Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
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supporting information
p. 7050 - 7054
(2018/10/17)
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- Copper-catalyzed synthesis of 2-aminobenzothiazoles from 2-iodophenyl isocyanides, potassium sulfide and amines
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A simple and practically useful synthetic method for the synthesis of a variety of 2-aminobenzothiazoles was developed. This methodology could construct one C-N bond and two C-S bonds in a step reaction and provide the desired products in good to perfect yields.
- Min, Hao,Xiao, Genhua,Liu, Wenjuan,Liang, Yun
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supporting information
p. 11088 - 11091
(2016/12/09)
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- Domino Suzuki coupling and condensation reaction: An efficient strategy towards synthesis of phenanthridines
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A short and convenient hetero-annulation protocol has been developed for the synthesis of substituted phenanthridines via domino Suzuki coupling and condensation between N-(2-iodo-aryl)-formamide derivatives and 2-formylphenylboronic acid in the presence of Pd(OAc)2, Cs2CO3 and PPh3 as catalytic system in dry DMF at 85-90 °C for 6-7 h. The intermediate after Suzuki coupling and deprotection of nitrogen under the same catalytic system, furnishes the corresponding phenanthridines in good yields after immediate condensation and dehydration.
- Ghosh, Munmun,Ahmed, Atiur,Singha, Raju,Ray, Jayanta K.
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supporting information
p. 353 - 355
(2015/03/05)
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- A Mild Approach for the Synthesis of Indoles from N -(2-Iodo-aryl)formAamides and Phenylacetylene by a Copper(I)- and Palladium-Catalyzed Cascade Process
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An efficient one-pot copper(I)- and palladium-catalyzed synthesis of indoles from N-(2-iodo-aryl)formamides and phenylAacetylene is described. The cascade reaction comprises a Sonogashira cross-coupling, an intramolecular C-N bond formation, and hydrolysi
- Ahmed, Atiur,Ghosh, Munmun,Dhara, Shubhendu,Ray, Jayanta K.
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supporting information
p. 2455 - 2458
(2015/07/27)
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- Synthesis of 3,1-Benzothiazines by Cyclisation of 2- Thioformylaminodiphenylacetylenes
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2-Formylaminodiphenylacetylenes, obtained in excellent yield by Sonogashira coupling of (2-iodoaryl)formamides with phenylacetylene, were thionated with P4S10 in boiling THF to give 2-thioformylaminodiphenylacetylenes. These acetylenes were cyclised by DBU at ambient temperature to give (4Z)-4-benzylidene-4H-3,1-benzothiazines and small amounts of 2-phenylindoles. The structures of (4Z)-4-benzylidene-6,8-dichloro- 4H-3,1-benzothiazine and 3,5-dichloro-2-thioformylaminodiphenylacetylene were established by single crystal X-ray analysis.
- Fernandes, Manuel A.,Reid, David H.
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p. 2231 - 2233
(2007/10/03)
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