The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions.
نویسندگان
چکیده
The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.
منابع مشابه
Diels–Alder [4+2] Cycloadditions of C20 with Some Diene and 1,2- Dioxo Compounds: A Theoretical Study
Diels–Alder [2+4] cycloaddition products of the reaction between C20 and C4H4X2 or C2O2X2 (X = H, F, Cl, CH3, NH2, NO2, and OH) were studied atB3LYP level of theory with 6-31G, 6-31G(d, p) and 6-311G(d, p) basis...
متن کاملبررسی تجربی و محاسباتی سنتز پلی یورتان های ترمیم پذیر بر پایه HTPB با استفاده از واکنش دیلز- آلدر فوران/مالئیمید
The reversibility of the Diels-Alder reaction can be used advantageously in polyurethane materials to endow them with recyclable, thermally reversible properties and self-healing ability to expand their application range. In this paper, linear and crosslink polyurethanes based on HTPB, which exhibit thermal reversibility through Diels-Alder and retro Diels-Alder reactions, were prepared and cha...
متن کاملHighly Regio- and Stereoselective Diels-Alder Cycloadditions via Two-Step and Multicomponent Reactions Promoted by Infrared Irradiation under Solvent-Free Conditions
Infrared irradiation promoted the Diels-Alder cycloadditions of exo-2-oxazolidinone dienes 1-3 with the Knoevenagel adducts 4-6, as dienophiles, leading to the synthesis of new 3,5-diphenyltetrahydrobenzo[d]oxazol-2-one derivatives (7, 9, 11 and 13-17), under solvent-free conditions. These cycloadditions were performed with good regio- and stereoselectivity, favoring the para-endo cycloadducts....
متن کاملMicrowave assisted green synthesis of α, ά- bis (substituted- benzylidene) alkanones
Microwave assisted green synthesis of α, ά- bis (substituted- benzylidene) alkanones by the crossed- aldol condensation reaction of substituted aryl aldehydes with ketones in the presence of catalytic amount of NbCl5 in good to excellent yields. This reaction is carried out under solvent-free conditions. The results showed that aldehydes bearing electron–donating substituent's on phenyl-ring fa...
متن کاملDiels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position acting as dienophiles with dienes.
Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1,3-butadienes (2a,b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examine...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 24 شماره
صفحات -
تاریخ انتشار 2010