Design and application of intramolecular arylogous nitroaldol condensation to access 2-aryl-benzofuran and -indole derivatives and formal synthesis of saprisartan DOI Creative Commons

Manyam Subbi Reddy,

Killari Satyam,

Surisetti Suresh

и другие.

RSC Advances, Год журнала: 2024, Номер 14(50), С. 37234 - 37239

Опубликована: Янв. 1, 2024

An intramolecular arylogous nitroaldol condensation has been developed for the synthesis of benzoheterols under transition metal-free conditions and synthesized an advanced key intermediate saprisartan—thus constituting a formal synthesis.

Язык: Английский

Design and Development of Carbene-Catalyzed Intramolecular Vinylogous Stetter Reaction to Access Phenanthrol Derivatives DOI

Purna Chandra Behera,

Jakkula Ramarao,

Surisetti Suresh

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 4, 2025

The present study reveals the design and development of an N-heterocyclic carbene (NHC)-catalyzed intramolecular vinylogous Stetter reaction. This protocol enabled synthesis diverse phenanthrol derivatives naphthol-fused heterocycles in very good to excellent yields. success title reaction relies on biaryl aldehydes bearing p-quinone methide (p-QM) moiety that acts as a (1,6-conjugate) acceptor while aldehyde functional group serves acyl anion equivalent, generated situ from NHC-catalyzed umpolung. Salient features presented include atom efficiency, operational simplicity, broad substrate scope, large-scale synthesis, postsynthetic modifications.

Язык: Английский

Процитировано

1
Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control DOI

Tanawat Phumjan,

Tomohiro Yazawa,

Shinji Harada

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 4, 2025

A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)3 as a Lewis acidic reagent. This method demonstrates broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, provides versatile route to complex nitrogen-containing scaffolds potential applications in medicinal chemistry total synthesis biologically active compounds.

Язык: Английский

Процитировано

0
A Formal [4+1] Annulation incorporating Styrylogous Aldol Condensation to Access Substituted 2-Styryl-benzofurans DOI

Manyam Subbi Reddy,

K. Kamala,

Surisetti Suresh

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A styrylogous aldol condensation has been introduced, constructing 2-styryl-benzofurans in high yields. The method's application demonstrated the efficient syntheses of biologically active aminostyryl-benzofurans good overall

Язык: Английский

Процитировано

0
NHC-Catalyzed Allylation of Aldehydes with MBH Carbonates and Their Michael Addition–Elimination-Cope Rearrangement Cascade: A Route to rac-Sacubitril DOI

Tushar B. Kale,

Sayali G. Jagtap,

Santosh B. Mhaske

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

We report herein a novel NHC-catalyzed transition-metal-free chemoselective allylation of aldehydes with Morita-Baylis-Hillman (MBH) carbonates using an inorganic base. Fascinatingly, the use organic base follows different mechanism, leading to highly functionalized 1,5-dienes via Michael addition-elimination reaction followed by [3,3]-sigmatropic Cope rearrangement. The described method harnesses new Csp2-Csp3 bond access α-methylene-γ-oxo-γ-substituted ester derivatives paving way facile synthesis potent natural products and active pharmaceutical ingredients (APIs). A broad range aromatic aliphatic MBH was employed provide variety interesting butanoate dienyl ketone scaffolds in good excellent yields. This chemistry has been extended efficient syntheses rac-sacubitril API γ-butyrolactone scaffold, which is privileged core present many APIs.

Язык: Английский

Процитировано

0
Design and application of intramolecular arylogous nitroaldol condensation to access 2-aryl-benzofuran and -indole derivatives and formal synthesis of saprisartan DOI Creative Commons

Manyam Subbi Reddy,

Killari Satyam,

Surisetti Suresh

и другие.

RSC Advances, Год журнала: 2024, Номер 14(50), С. 37234 - 37239

Опубликована: Янв. 1, 2024

An intramolecular arylogous nitroaldol condensation has been developed for the synthesis of benzoheterols under transition metal-free conditions and synthesized an advanced key intermediate saprisartan—thus constituting a formal synthesis.

Язык: Английский

Процитировано

2