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

2015 ◽  
Vol 11 ◽  
pp. 1514-1519 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Ajay Kumar Chinnam ◽  
Mukesh Eknathrao Shirbhate

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

2018 ◽  
Vol 14 ◽  
pp. 2537-2544 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Saidulu Todeti ◽  
Vikas R Aswar

We have developed an efficient synthetic strategy to assemble C 3-symmetric molecules containing propellane moieties as end groups and a benzene ring as a central core. The synthesis of these C 3-symmetric molecules involves simple starting materials. Our approach to C 3-symmetric compounds relies on a Diels–Alder reaction, cyclotrimerization and ring-closing metathesis as key steps.


2016 ◽  
Vol 57 (50) ◽  
pp. 5605-5607 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Rao Cheekatla ◽  
Ajay Kumar Chinnam ◽  
Tanu Jain

2015 ◽  
Vol 11 ◽  
pp. 1367-1372 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Mohammad Saifuddin ◽  
Rashid Ali ◽  
Gaddamedi Sreevani

A simple synthetic strategy to C 2-symmetric bis-spiro-pyrano cage compound 7 involving ring-closing metathesis is reported. The hexacyclic dione 10 was prepared from simple and readily available starting materials such as 1,4-naphthoquinone and cyclopentadiene. The synthesis of an unprecedented octacyclic cage compound through intramolecular Diels–Alder (DA) reaction as a key step is described. The structures of three new cage compounds 7, 12 and 18 were confirmed by single crystal X-ray diffraction studies.


Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5339-5350 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Cheekatla ◽  
Darshan Mhatre

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.


Synthesis ◽  
2019 ◽  
Vol 51 (21) ◽  
pp. 3989-3997 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Ramakrishna Reddy Keesari ◽  
Saima Ansari

Herein, we describe a simple synthetic strategy to assemble aza-polyquinane systems containing an indole motif by employing the Fischer indolization and ring-rearrangement metathesis as key steps. The precursor used here is exo-dicyclopentadienone, which is derived from less explored exo-dicyclopentadiene. By using this approach, several aza-polyquinanes that contain indole units and fused medium rings (eight- and nine-membered rings) were synthesized in good yields.


2015 ◽  
Vol 11 ◽  
pp. 1373-1378 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Rama Gunta

Here, we describe a new and simple synthetic strategy to various polycyclic sulfones via Diels–Alder reaction and ring-rearrangement metathesis (RRM) as the key steps. This approach delivers tri- and tetracyclic sulfones with six (n = 1), seven (n = 2) or eight-membered (n = 3) fused-ring systems containing trans-ring junctions unlike the conventional all cis-ring junctions generally obtained during the RRM sequence. Interestingly the starting materials used are simple and commercially available.


2014 ◽  
Vol 10 ◽  
pp. 2664-2670 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Mirtunjay Kumar Dipak

Intricate caged molecular frameworks are assembled by an atom economical process via a Diels–Alder (DA) reaction, a Claisen rearrangement, a ring-closing metathesis (RCM) and an alkenyl Grignard addition. The introduction of olefinic moieties in the pentacycloundecane (PCUD) framework at appropriate positions followed by RCM led to the formation of novel heptacyclic cage systems.


2015 ◽  
Vol 11 ◽  
pp. 1259-1264 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Ongolu Ravikumar

Atom efficient processes such as the Diels–Alder reaction (DA) and the ring-rearrangement metathesis (RRM) have been used to design new polycycles. In this regard, ruthenium alkylidene catalysts are effective in realizing the RRM of bis-norbornene derivatives prepared by DA reaction and Grignard addition. Here, fused polycycles are assembled which are difficult to produce by conventional synthetic routes.


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