13141-39-4Relevant academic research and scientific papers
Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
La-Ongthong, Kannika,Naweephattana, Phiphop,Khaikate, Onnicha,Surawatanawong, Panida,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Kuhakarn, Chutima
, p. 6338 - 6351 (2020/07/21)
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.
Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives
Khaikate, Onnicha,Inthalaeng, Natthamon,Meesin, Jatuporn,Kantarod, Kritchasorn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Leowanawat, Pawaret,Kuhakarn, Chutima
, (2019/11/29)
A new synthetic approach for the synthesis of indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines has been developed by employing the freshly prepared o-alkynylisocyanobenzenes derived from o-alkynylformamide derivatives as substrates. The synthetic transformations involved chloride-ion-triggered 6-endo cyclization of o-alkynylisocyanobenzenes to generate 2-chloroquinolines in situ, which further cyclized intramolecularly with nitrogen or sulfur atom via a cascade process to provide the corresponding indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines, respectively, in moderate to excellent yields.
Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines
Khaikate, Onnicha,Soorukram, Darunee,Leowanawat, Pawaret,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
, p. 7050 - 7057 (2019/11/11)
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.
Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions
Mutra, Mohana Reddy,Dhandabani, Ganesh Kumar,Wang, Jeh-Jeng
supporting information, p. 3960 - 3968 (2018/09/10)
A new synthetic protocol has been developed for the synthesis of N-formamide derivatives using ethers as a C1 synthon under metal-free reaction conditions. The reaction is proposed to proceed through C?H functionalization, C?O cleavage, and C?N bond formation. This protocol is applicable to a variety of primary amines resulting in N-formamides in moderate to good yields. 1,4-dioxane was chosen as best C1 synthon after screening with various ethers. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. While using α-amino ketones a α-alkylation product was formed rather than formylation. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives in moderate yields. (Figure presented.).
Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 7050 - 7054 (2018/10/17)
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.
Sulfinates and thiocyanates triggered 6-endo cyclization of o-alkynylisocyanobenzenes
Khaikate, Onnicha,Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 8553 - 8558 (2018/12/01)
Diverse 2-sulfonyl- and 2-thiocyanato-3-substituted quinolines were synthesized from o-alkynylisocyanobenzenes by nucleophilic addition of the respective sulfinate sodium salts and ammonium thiocyanate to the isocyanide moiety followed by cyclization. The salient features of the methodology include metal-free, ambient temperature and mild reaction conditions, ease of reagent handling, and broad functional group tolerance.
Synthesis of 3-acyl-2-arylindole via palladium-catalyzed isocyanide insertion and oxypalladation of alkyne
Nanjo, Takeshi,Yamamoto, Sho,Tsukano, Chihiro,Takemoto, Yoshiji
supporting information, p. 3754 - 3757 (2013/08/23)
The synthesis of 3-acyl-2-arylindole derivatives was performed through palladium-catalyzed isocyanide insertion and oxypalladation of an alkyne. As a result of the introduction of internal nucleophiles, domino cyclization was also achieved for the synthes
Synthesis of 2-alkoxy(aroxy)-3-substituted Quinolines by DABCO-promoted cyclization of o-alkynylaryl isocyanides
Zhao, Jiaji,Peng, Changlan,Liu, Lanying,Wang, Yong,Zhu, Qiang
supporting information; experimental part, p. 7502 - 7504 (2011/02/21)
Diversified 2-alkoxy- and 2-aroxy-3-substituted quinolines were synthesized from o-alkynylaryl isocyanides and alcohols and phenols promoted by DABCO, respectively. The reaction was initiated by nucleophilic addition of DABCO to isocyanide and subsequent
Synthesis of 2-halogenated quinolines by halide-mediated intramolecular cyclization of o-alkynylaryl isocyanides
Mitamura, Takenori,Nomoto, Akihiro,Sonoda, Motohiro,Ogawa, Akiya
supporting information; experimental part, p. 822 - 824 (2010/09/06)
When o-alkynylaryl isocyanides 1 are treated with triethylamine in chloroform, intramolecular chlorinating cyclization of the isocyanides takes place, affording the corresponding 2-chlorinated quinoline derivatives 2 in good to excellent yields, selective
Synthesis of 3,1-Benzothiazines by Cyclisation of 2- Thioformylaminodiphenylacetylenes
Fernandes, Manuel A.,Reid, David H.
, p. 2231 - 2233 (2007/10/03)
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.
