Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps

Kotha, Sambasivarao; Chinnam, Ajay Kumar; Shirbhate, Mukesh E.

doi:10.3762/bjoc.11.165

Cited by 18 publications

(10 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Keeping the importance of C 3 -symmetric molecules in medicinal and bioorganic chemistry besides their vital role in material science and technology, the same group has also prepared star-shaped C 3 -symmetric compounds 45 and 46 involving cyclotrimerization and DMU/TA mediated indolization approach (Figure 4) [36]. Furthermore, as can be inspected from the Figure 5, they design and constructed varied cyclophane derivatives (48, 49, 54, 55 and 59) through the involvement of the Grignard reaction, RCM and a low melting mixture mediated indolization sequences in respectable yields because of their applicability in supramolecular chemistry [37][38][39][40][41]. In addition to these, Kotha's group has also prepared diverse polycyclic mono-(50, 56, 63) and bis-indole derivatives (51, 57, 58, 64) by means of a deep eutectic mixture of DMU/ TA (70:30) under operationally simple reaction conditions [42][43][44][45].…”

Section: Construction Of Indole Systems Under a Low Melting Mixture Of Dmu/tamentioning

confidence: 99%

Low Melting Mixture of L-(+)-Tartaric Acid and N,N′-Dimethyl Urea: A New Arrival in the Green Organic Synthesis

Ali¹

2021

Current Topics in Chirality - From Chemistry to Biology

View full text Add to dashboard Cite

After the first report of deep eutectic mixtures by the team of Abbott in 2003, the advent of green synthesis has been progressively changing the way synthetic chemistry is thought and also taught. Since then, a plethora of efforts worldwide have been taken to stretch the ideas of sustainable as well as environmentally benign approaches to do the crucial synthetic organic transformations under operationally simple yet effective conditions. Although, till date, several green synthetic strategies for examples ultrasound, microwaves, flow as well as grindstone chemistry etc., and green reaction media (e.g. ionic liquid, water, scCO2, and so forth) have successfully been invented. But a low melting mixture of L-(+)-tartaric acid (TA) and N,N′-dimethylurea (DMU), usually plays a double and/or triple role (solvent, catalyst, and/or reagent), though still infancy but enjoys several eye-catching properties like biodegradability, recyclability, non-toxicity, good thermal stability, tunable physiochemical properties, low vapor pressure as well as reasonable prices in addition to the easy preparation with wide functional groups tolerance. To this context, keeping the importance of this novel low melting mixture in mind, we intended to reveal the advancements taken place in this wonderful area of research since its first report by the Köenig’s group in 2011 to till date. In this particular chapter, firstly we would disclose the importance of the green synthesis followed by a brief description of deep-eutectic solvents (DESs) particularly emphasizing on the role of L-(+)-TA and DMU from modern synthetic chemistry perspective.

show abstract

Section: Construction Of Indole Systems Under a Low Melting Mixture Of Dmu/tamentioning

confidence: 99%

Low Melting Mixture of L-(+)-Tartaric Acid and N,N′-Dimethyl Urea: A New Arrival in the Green Organic Synthesis

Ali¹

2021

Current Topics in Chirality - From Chemistry to Biology

View full text Add to dashboard Cite

show abstract

“…Recently, Kotha and co‐workers reported the synthesis of thiophene and indole containing hybrid cyclophane derivative 76 by applying the FI and RCM in alliance . The required building block 73 was obtained in a two‐step sequence starting with a readily available 2,5‐thiophenedicarboxaldehyde ( 71 ).…”

Section: Cyclophanesmentioning

confidence: 99%

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Kotha

Meshram

Dommaraju

2018

The Chemical Record

Self Cite

View full text Add to dashboard Cite

In this perspective, we summarize new synthetic approaches for the construction of various polycyclic compounds involving ring-closing metathesis as a key step. In this regard, we used ring-closing metathesis in combination with other popular reactions like Suzuki-Miyaura coupling, Claisen rearrangement, Fischer indolization, Grignard addition, Diels-Alder reaction, and [2+2] cycloaddition reaction etc. To this end, a variety of functional molecules such as α-amino acids, cyclophanes, heterocycles, propellanes, spirocycles, and macrocycles have been prepared. The strategies developed and the molecules prepared here play a key role in designing new materials and also act as lead compounds in drug design. The strategies and tactics developed here are useful to design polycycles, macrocycles, and heterocycles of diverse ring systems.

show abstract

“…Similarly, thiophene‐2,5‐dicarbaldehyde 79 , was treated with the Grignard reagent such as 4‐pentenylmagnesium bromide to generate the diol 80 (52 %). Later, the diol 80 was subjected to MnO 2 oxidation in CH 2 Cl 2 to deliver the dione 81 (73 %), which was then treated with Grubb's catalyst to accomplish the RCM sequence.…”

Section: Applications Of Fimentioning

confidence: 99%

“…Next, the dione 86 subjected to FI with 1‐methyl‐1‐phenylhydrazine 10 to deliver the bis‐indole product 88 (70 %). Finally, the bis‐indole derivative 88 on treatment with G‐II catalyst gave the cyclized product 89 in 93 % yield (Scheme ) …”

Section: Applications Of Fimentioning

confidence: 99%

Application of Fischer Indolization under Green Conditions using Deep Eutectic Solvents

Kotha

Chakkapalli

2017

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Indole and its derivatives captured the attention of organic chemists due to their applications in medicinal chemistry. The examples covered here are intricate polycyclic indole derivatives and these include: azapolyquinanes, cyclophanes, spirocycles and other heterocycles. We found that deep eutectic mixture such as L-(+)-tartaric acid (TA) and dimethyl urea (DMU) is useful to prepare complex unnatural indole derivatives. These conditions from time to time produced indole derivatives which are not possible by conventional methods. Various substrates containing multiple carbonyl groups were shown to undergo Fischer indolization (FI) in deep eutectic mixtures and thus expand its scope to a higher level.

show abstract

Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps

Abstract: SummaryWe demonstrate a new synthetic strategy to cyclophanes containing thiophene and indole moieties via Grignard addition, Fischer indolization and ring-closing metathesis as key steps.

Cited by 18 publications

References 37 publications

Low Melting Mixture of L-(+)-Tartaric Acid and N,N′-Dimethyl Urea: A New Arrival in the Green Organic Synthesis

Low Melting Mixture of L-(+)-Tartaric Acid and N,N′-Dimethyl Urea: A New Arrival in the Green Organic Synthesis

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Application of Fischer Indolization under Green Conditions using Deep Eutectic Solvents

Contact Info

Product

Resources

About