Tandem-Michael-cyclization cascade to make pyridines: Use of electron-deficient acetylenes for the synthesis of indolizines in aqueous media

Synthesis, characterization, and anti‐inflammatory properties of novel ethyl 3‐benzoyl‐7‐(trifluoromethyl)indolizine‐1‐carboxylate derivatives: In silico and in vitro analysis

“…Heterocyclic compounds are of great interest in organic chemistry, having various applications in natural products and synthetic pharmaceuticals (Dorai et al, 2023;Ningegowda et al, 2020;Uppar et al, 2021;Uppar, Mudnakudu-Nagaraju, et al, 2020;Venugopala et al, 2020). Indolizine is a bridged nitrogen-containing bicyclic heterocyclic moiety (de Souza et al, 2016;Lakshmikanth et al, 2023;Sumanth et al, 2023). It is a 10π electron conjugated planar electronic structure, also known as a bioisostere of indole (Sandeep et al, 2013a(Sandeep et al, , 2014Shivaprasad et al, 2023;Sumanth et al, 2023;Venugopala et al, 2018).…”

Design, synthesis and characterization of ethyl 3‐benzoyl‐7‐morpholinoindolizine‐1‐carboxylate as anti‐tubercular agents: In silico screening for possible target identification

“…This study is a continuation of our research work in the design and preparation of the nitrogen‐containing heterocyclic compound ‘Indolizine’ as an anti‐TB agent. Indolizines are prime focussed due to their interest in synthetic chemistry (Lakshmikanth et al., 2023; Sandeep et al., 2013a, 2014; Sumanth et al., 2023; Venugopala et al., 2018) with medicinal applications like tuberculosis (Khedr et al., 2018; Sandeep Chandrashekharappa et al., 2019; Venugopala, Chandrashekharappa, Pillay, et al., 2019; Venugopala, Tratrat, Chandrashekharappa, et al., 2019; Venugopala, Tratrat, Pillay, et al., 2019), antioxidant (Vijayakumar Uppar, 2020), anticancer (Sandeep, Padmashali, et al., 2016), anti‐microbial (Sandeep et al., 2013b; Uppar et al., 2021; Vijayakumar Uppar, 2020), anti‐inflammatory (Chandrashekharappa, Venugopala, Tratrat, et al., 2018; Sandeep et al., 2017; Venugopala, Al‐Attraqchi, Tratrat, et al., 2019; Venugopala, Chandrashekharappa, Tratrat, et al., 2021), larvicidal (Chandrashekharappa, Venugopala, Nayak, et al., 2018; Sandeep, Venugopala, et al., 2016; Uppar et al., 2020) and NmeNANAS inhibitor (Alwassil et al., 2019). In this work, we have designed, characterized and evaluated a series of morpholine‐containing indolizine derivatives (5a‐o) (Table 1) for their anti‐tubercular potential.…”

Efficient One‐Pot Multicomponent Approach to 3‐Phenylpyrrolo[1,2‐a]Pyrazine and Novel 3‐Phenylpyrazino[1,2‐a]Indole in Aqueous Medium

“…Building upon this prior research, we aimed to develop an efficient one‐pot synthetic protocol for the synthesis of 3‐phenylpyrrolo[1,2‐ a ]pyrazine and novel 3‐phenylpyrazino[1,2‐ a ]indole by novel reaction mechanism and mild reaction condition via greener approach [11] . The reaction involved a one‐pot three‐component reaction under suitable conditions, utilizing aqueous ammonium hydroxide and various substituted 2‐bromo‐acetophenones or α‐bromo ketones (phenacyl bromides) with 1 H ‐pyrrole‐2‐carbaldehyde with good to excellent yield.…”

“…Building upon this prior research, we aimed to develop an efficient one-pot synthetic protocol for the synthesis of 3phenylpyrrolo[1,2-a]pyrazine and novel 3-phenylpyrazino[1,2a]indole by novel reaction mechanism and mild reaction condition via greener approach. [11] The reaction involved a onepot three-component reaction under suitable conditions, utilizing aqueous ammonium hydroxide and various substituted 2bromo-acetophenones or α-bromo ketones (phenacyl bromides) with 1H-pyrrole-2-carbaldehyde with good to excellent yield. In the present study, we hypothesized that phenacyl bromides would undergo a condensation-induced annulation process that begins with nitrogen intermediate creation (Nalkylation), continues with ammonium hydroxide addition to imine synthesis, and concludes with condensation.…”