Investigation of the Acid-Mediated Cyclisation of Amide Acetal for the Synthesis of Benzazepinone

Heterocycles ◽  
2008 ◽  
Vol 75 (8) ◽  
pp. 1963 ◽  
Author(s):  
Somsak Ruchirawat ◽  
Wong Phakhodee ◽  
Poolsak Sahakitpichan ◽  
Songpon Deechongkit
Keyword(s):  
Amide Acetal

scholarly journals Concatenated Batch and Continuous Flow Procedures for the Upgrading of Glycerol-Derived Aminodiols via N-Acetylation and Acetalization Reactions

Catalysts ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 21
Author(s):  
Davide Rigo ◽  
Nadia Alessandra Carmo Dos Santos ◽  
Alvise Perosa ◽  
Maurizio Selva
Keyword(s):  
Continuous Flow ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Catalyst Free ◽  
Amide Derivatives ◽  
Amide Acetal ◽  
Enol Ester ◽  
Isopropenyl Acetate

An unprecedented two-step sequence was designed by combining batch and continuous flow (CF) protocols for the upgrading of two aminodiol regioisomers derived from glycerol, i.e., 3-amino-1,2-propanediol and 2-amino-1,3-propanediol (serinol). Under batch conditions, at 80–90 °C, both substrates were quantitatively converted into the corresponding amides through a catalyst-free N-acetylation reaction mediated by an innocuous enol ester as isopropenyl acetate (iPAc). Thereafter, at 30–100 °C and 1–10 atm, the amide derivatives underwent a selective CF-acetalisation in the presence of acetone and a solid acid catalyst, to afford the double-functionalized (amide-acetal) products.

ChemInform Abstract: A Chemoselective, Acid-Mediated Conversion of Amide Acetal to Oxazole: The Key Step in the Synthesis of Cardiovascular Drug, Ifetroban Sodium.

ChemInform ◽  
2010 ◽  
Vol 29 (39) ◽  
pp. no-no
Author(s):  
S. SWAMINATHAN ◽  
A. K. SINGH ◽  
W.-S. LI ◽  
J. J. VENIT ◽  
K. J. JUN. NATALIE ◽  
...  
Keyword(s):  
Cardiovascular Drug ◽  
Amide Acetal

Synthesis of 2-Methylpyrrolo[1,2-a]pyrazin-1(2h)-one

1988 ◽  
Vol 41 (10) ◽  
pp. 1583 ◽  
Author(s):  
MA Brimble ◽  
MT Brimble ◽  
R Hodges ◽  
GA Lane
Keyword(s):  
Lewis Acid ◽  
Feeding Deterrent ◽  
Insect Feeding ◽  
Amide Acetal

The synthesis of 2-methylpyrrolo[1,2-a]pyrazin-1(2H)-one (2) present in the insect feeding deterrent peramine (1) through oxidation of the saturated lactam (3) is described. The preparation of the related 6- methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (12) through a Lewis-acid- catalysed cyclization of the amide acetal (7) is also described.

Amide acetal Claisen rearrangement in the synthesis of mesembrane alkaloids

1991 ◽  
pp. 561 ◽  
Author(s):  
Sieglinde Bauermeister ◽  
Izebrandt D. Gouws ◽  
Heinrich F. Strauss ◽  
Elise M. M. Venter
Keyword(s):  
Claisen Rearrangement ◽  
Amide Acetal

A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium

1998 ◽  
Vol 39 (27) ◽  
pp. 4769-4772 ◽  
Author(s):  
Shankar Swaminathan ◽  
Ambarish K. Singh ◽  
Wen-Sen Li ◽  
John J. Venit ◽  
Kenneth J. Natalie ◽  
...  
Keyword(s):  
Cardiovascular Drug ◽  
Amide Acetal

Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions

2017 ◽  
Vol 6 (5) ◽  
pp. 520-526 ◽  
Author(s):  
Yongseok Kwon ◽  
Jaehyun Jung ◽  
Jae Hyun Kim ◽  
Woo-Jung Kim ◽  
Sanghee Kim
Keyword(s):  
Allylic Alcohols ◽  
Amide Acetal ◽  
Palladium Catalyzed ◽  
Neutral Conditions

Orthoamide und Iminiumsalze, LXXXI [1]. Orthoamid-Derivate der 1,3-Dimethylparabansäure / Orthoamides and Iminium Salts LXXXI [1]. Orthoamide Derivatives of 1,3-Dimethylparabanic Acid

2012 ◽  
Vol 67 (9) ◽  
pp. 907-912
Author(s):  
Willi Kantlehner ◽  
Erwin Haug ◽  
Christophe Bauer
Keyword(s):  
Hydrogen Chloride ◽  
Dimethyl Sulfate ◽  
One Pot ◽  
Sodium Methanolate ◽  
Iminium Salts ◽  
Iminium Salt ◽  
Amide Acetal ◽  
Derivatives Of ◽  
Subsequent Addition

1,3-Dimethyl-5-imino-imidazolidine-2,4-dione (7a) undergoes thiolysis (H2S) to give the corresponding imidazolidine-2,4-dione-5-thione derivative 6. The 5-N-methylimino analogue 7b can be obtained from 7a by methylation. Further methylation of 7b affords the crude iminium salt 8c from which the heterocyclic orthoamide derivatives 10, 11 can be prepared. The heterocyclic amide acetal 9a can be obtained from 7a and dimethyl sulfate in methanol and subsequent addition of sodium methanolate in a one-pot reaction. The aminal ester 10 is converted to the amide acetal 9a on treatment with hydrogen chloride in methanol

Sign in / Sign up

Export Citation Format

Share Document