91633-32-8Relevant academic research and scientific papers
Design, Synthesis, and Biological Evaluation of Substituted 4,6-Dihydrospiro[[1,2,3]triazolo[4,5- b]pyridine-7,3′-indoline]-2′,5(3 H)-dione Analogues as Potent NS4B Inhibitors for the Treatment of Dengue Virus Infection
Xu, Jimin,Xie, Xuping,Ye, Na,Zou, Jing,Chen, Haiying,White, Mark A.,Shi, Pei-Yong,Zhou, Jia
, p. 7941 - 7960 (2019)
A series of substituted 4,6-dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3′-indoline]-2′,5(3H)-dione analogues were synthesized and evaluated as potent dengue virus inhibitors. Throughout a structure-activity relationship exploration on the amide of the
Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 1179 - 1183 (2021/02/01)
We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.
SUBSTITUTED 4,6-DIHYDROSPIRO[[1,2,3]TRIAZOLO[4,5-B]PYRIDINE-7,3'-INDOLINE]-2',5(3H)-DIONE ANALOGUES
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, (2021/02/19)
A series of substituted 4,6-dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3′-indoline]-2′,5(3H)-dione analogues, the use thereof and the preparation thereof.
Recyclable zinc (II) ionic liquid catalyzed synthesis of azides by direct azidation of alcohols using trimethylsilylazide at room temperature
Singh, Ashima,Singh, Harjinder,Khurana
supporting information, p. 2498 - 2502 (2017/05/31)
A new efficient method has been reported for the synthesis of azides by direct azidation of alcohols with TMSN3 in presence of recyclable task specific ionic liquid (TSIL) [bmim]ZnCl3 as a catalyst in DCM at room temperature. Ionic liquid [bmim]ZnCl3 was synthesized under solvent free conditions and characterized by IR, 1H NMR, 13C NMR and HRMS. The Lewis acidity of catalyst was also examined using IR spectroscopy. The main features of this new methodology are high yields of products, recyclability of catalyst, scalability of reaction to gram scale and short reaction time.
Highly selective direct azidation of alcohols over a heterogeneous povidone-phosphotungstic solid acid catalyst
Kamble, Sumit,More, Sagar,Rode, Chandrashekhar
, p. 10240 - 10245 (2016/12/06)
A simple protocol for the selective azidation of alcohols is developed using a solid acid hybrid of a povidone and phosphotungstic acid (PVP-PWA) using azidotrimethylsilane as an azide source at room temperature. In a broad substrate scope, various activated as well as unactivated benzylic and diphenyl alcohols were treated smoothly with TMS-N3 to selectively produce only azide products with excellent yields in a very short reaction time of 2 h. FT-IR confirmed the stability of the catalyst with retention of the Keggins structure after the reaction. Recycling experiments demonstrated the reusability of the PVP-PWA (3?:?1) several times without losing its original activity.
Convenient and direct azidation of sec -benzyl alcohols by trimethylsilyl azide with bismuth(III) triflate catalyst
Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Thongaram, Phanida,Kaewmee, Benyapa
, (2015/01/30)
Sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.
Convenient and direct azidation of sec -benzyl alcohols by trimethylsilyl azide with bismuth(III) triflate catalyst
Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Thongaram, Phanida,Kaewmee, Benyapa
, p. 323 - 329 (2015/02/19)
Sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.
Chemoselective and direct functionalization of methyl benzyl ethers and unsymmetrical dibenzyl ethers by using iron trichloride
Sawama, Yoshinari,Goto, Ryota,Nagata, Saori,Shishido, Yuko,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 2631 - 2636 (2014/03/21)
Methyl and benzyl ethers are widely utilized as protected alcohols due to their chemical stability, such as the low reactivity of the methoxy and benzyloxy groups as leaving groups under nucleophilic conditions. We have established the direct azidation of chemically stable methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols. The present azidation chemoselectively proceeds at the secondary or tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers. Ethers exchanged: Methyl and benzyl ethers are chemically stable and generally tolerant under nucleophilic substitution conditions. Iron-catalyzed direct functionalizations (e.g., azidation, allylation, alkynylation, and cyanation) of methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols were established with excellent regioselectivities (see scheme; PG: protecting group; Bn: benzyl; Nu: nucleophile; TMS: trimethylsilyl). Copyright
SPIROPYRAZOLOPYRIDINE DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF VIRAL INFECTIONS
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, (2014/10/29)
A compound of Formula (I) is provided that has been shown to be useful for treating a disease caused by a viral infection: (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, X1, X2, X3 and X4, are as defined herein.
One-pot green synthesis of azides from alcohols using bronsted acidic ionic liquid [HMIM][BF4] as solvent and catalyst
Garg, Bhaskar,Ling, Yong-Chien
, p. 737 - 742 (2014/07/22)
Bronsted acidic ionic liquid, [HMIM][BF4], has been used as a non-volatile, eco-friendly solvent, and catalytic medium for the one-pot green synthesis of azides from corresponding alcohols. The [HMIM][BF 4] showed high reactivity than [BMIM][BF4] and [BMIM][PF6], affording azides in up to 97% yield, which could be easily separated from the reaction mixture. The ease of recyclability of [HMIM][BF4] makes the reaction economically and potentially viable for practical applications. Azides are versatile substrates in organic synthesis and serve as convenient intermediate in the synthesis of pharmaceutical heterocycles and natural products. By using dual functional [HMIM][BF 4] as solvent and catalyst, efficient synthesis of azides from their corresponding alcohols have been undertaken under eco-friendly conditions. This study may pave the way for practical application of [HMIM][BF4] in cholesterylamine synthesis.
