- Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
-
Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.
- Mahajani, Nivedita S.,Meador, Rowan I. L.,Smith, Tomas J.,Canarelli, Sarah E.,Adhikari, Arijit A.,Shah, Jigisha P.,Russo, Christopher M.,Wallach, Daniel R.,Howard, Kyle T.,Millimaci, Alexandra M.,Chisholm, John D.
-
p. 7871 - 7882
(2019/06/27)
-
- Copper-catalyzed cross-coupling of thiols, alcohols, and oxygen for the synthesis of esters
-
Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions.
- Lim, Seungyeon,Ji, Miran,Wang, Xi,Lee, Chan,Jang, Hye-Young
-
supporting information
p. 591 - 595
(2015/01/30)
-
- 5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions
-
5,5′-Dimethyl-3,3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated by filtration and recycled to its azoisoxazole by oxidation.
- Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush
-
supporting information; experimental part
p. 4436 - 4443
(2010/11/05)
-
- Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension
-
Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2′-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension.
- Ohno, Osamu,Ye, Mao,Koyama, Tomoyuki,Yazawa, Kazunaga,Mura, Emi,Matsumoto, Hiroshi,Ichino, Takao,Yamada, Kaoru,Nakamura, Kazuhiko,Ohno, Tomohiro,Yamaguchi, Kohji,Ishida, Junji,Fukamizu, Akiyoshi,Uemura, Daisuke
-
experimental part
p. 7843 - 7852
(2009/04/11)
-
- Efficient and selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and benzoates catalyzed by bismuth(III) salts
-
A variety of TMS and THP ethers are efficiently converted to their corresponding acetates and benzoates with acetic and benzoic anhydrides in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)3, and Bi(OTf)sub
- Mohammadpoor-Baltork, Iraj,Khosropour, Ahmad R.
-
p. 189 - 193
(2007/10/03)
-