+++Запрос в Reaxys & SF

[klamm]

Коллеги, приветствую Вас!
Хотелось бы посмотреть в базах данных два изомерных силилированных дифенилоксазола.
№1
CΣ(C)(C)C1=CC=C(C=C1)C1=NC=C(O1)C1=CC=CC=C1

1.mol

№2
CΣ(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)C1=CC=CC=C1

2.mol

Интересует синтез.

Спасибо!

[Arkadii_Tarasevych]

Добрый вечер. Обе структуры проверил в СкайФайндере. Результат 0. Если проводить поиск по схожим струкурам кое-что есть: 2,5-diphenyl-4-(trimethylsilyl)-oxazole и B-[4-(5-phenyl-2-oxazolyl)phenyl]-boronic acid. Вот ссылки, может сгодиться?!

1. Preparation of oxadiazolylphenylboronic acid derivatives and analogs for use as fatty acid amide hydrolase inhibitors By Behnke, Mark L.; Castro, Alfredo C.; Evans, Catherine A.; Grenier, Louis; Grogan, Michael J.; Liu, Tao; Snyder, Daniel A.; Tibbitts, Thomas T. From PCT Int. Appl. (2009), WO 2009126691 A1 20091015. Language: English, Database: CAPLUS
Title compds. I [each W independently = C, N, or CR12; X = covalent bond, O, S, C(O), etc.; Y = OH, OR3, (un)substituted alkyl, etc.; Z = OH or OR3; or Y and Z are taken together with the boron to which they are attached to form a ring contg. at least one O, S, N, or NR5 atom directly bonded to the boron atom; each R1 independently = halo, CF3, CN, NO2, etc.; R2 = H, halo, N3, CN, etc.; each R3 independently = (un)substituted alkyl, heteroalkyl, heterocyclyl, etc.; R5 = H, (un)substituted alkyl, heteroaryl, etc.; R12 = H, halo, CF3, etc.], and their pharmaceutically acceptable salts, are prepd. and disclosed as fatty acid amide hydrolase (FAAH) inhibitors. Thus, e.g., II was prepd. by cyclization of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazine with 3-(2-oxopyrrolidin-1-yl)propionic acid followed by hydrolysis. I were evaluated in human FAAH inhibition assays, e.g., II demonstrated a Ki value of 0.1 to 1 μM.

2. Product class 12: oxazoles By Boyd, G. V. From Science of Synthesis (2002), 11, 383-479. Language: English, Database: CAPLUS
A review of the synthesis of simple and condensed oxazoles. Reaction covered include addn., cycloaddn., heterocyclization, hydrolysis.
SubstancesReactions~9 Citings

3. Substituted oxazoles: syntheses via lithio intermediates By Whitney, Scott E.; Rickborn, Bruce From Journal of Organic Chemistry (1991), 56(9), 3058-63. Language: English, Database: CAPLUS
Reactions of 2-, 4-, and 5-lithiooxazoles are used to prep. varoius derivs. Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldehyde is described, and a rationale for this behavior is offered. Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with BuLi. Deprotonation of the ortho position of the 2-Ph group and addn. of Bu to the 2-position of the oxazole compete with the desired 4-lithiation. The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-2,5-diphenyloxazole. This intermediate has been converted to the 4-bromo, -Me, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivs. Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position. Deprotonation of 2-alkoxyoxazoles occurs at the α-carbon in preference to ring sites. Further reaction of a 2-(phenylmethanol) methoxymethyl ether I with base and acetyl chloride leads to an acyloin deriv. II. Chromic acid oxidn. is used to prep. both 2- and 4-benzoyloxazoles. The formation of a 2-ethoxyoxazole III from the 2-oxazolone IV via Meerwein salt chem. is described.

[klamm]

Arkadii_Tarasevych, спасибо большое за помощь!