A simple approach to bis-spirocycles and spiroindole derivatives via green methods such as Fischer indolization, ring-closing metathesis, and Suzuki--Miyaura cross-coupling

We have developed a simple synthetic methodology for bis-spirocycles and spiroindole derivatives starting with a commercially available 6-bromo-2-tetralone. Here, we have used Fischer indolization, ring-closing metathesis, and Suzuki--Miyaura cross-coupling as key steps to assemble a variety of spirocyclic frameworks. The methodology developed here is simple and it may be useful to prepare various spirocycles containing indole moiety.

A simple approach to bis-spirocycles and spiroindole derivatives via green methods such as Fischer indolization, ring-closing metathesis, and Suzuki--Miyaura cross-coupling

We have developed a simple synthetic methodology for bis-spirocycles and spiroindole derivatives starting with a commercially available 6-bromo-2-tetralone. Here, we have used Fischer indolization, ring-closing metathesis, and Suzuki--Miyaura cross-coupling as key steps to assemble a variety of spirocyclic frameworks. The methodology developed here is simple and it may be useful to prepare various spirocycles containing indole moiety.Generating molecular complexity from simple and readily available starting materials has received a great deal of attention from synthetic chemists. Suzuki coupling and its related processes provide intricate molecular architectures by transforming the C−X bond into a new C−C bond under operationally simple reaction conditions. 1−10 In recent years, spirocycles 11−21 have been found to be useful building blocks in preparative organic chemistry for the construction of theoretically as well as biologically interesting targets. The structures of some biologically important substances (1–6) containing the spiro-linkage are shown in Figure 1. 22,23 In this context, development of simple and green protocols involving short synthetic sequences and minimum amounts of byproducts is highly desirable.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

The synthesis, characterization, and catalytic properties of (2-C,N) palladacycles with N-heterocyclic carbene-based ancillary ligands

Muhammet Emin GÜNAY, Rukiye FIRINCI, Gülcan Gençay ÇOĞAŞLIOĞLU

Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions

MAHMUT ULUSOY, NURDAL ÖNCEL, Emine AYTAR

New Pd(II) and Pt(II)-diaminophosphine complexes bearing cyclohexyl or isopropyl moiety: use of Pd(II) complexes as precatalyst in Mizoroki{Heck and Suzuki{Miyaura cross-coupling reactions

Akın BAYSAL, Feyyaz DURAP, Murat AYDEMİR

Efficient C{C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

Seyedeh Simin MIRI, Fatemeh ASHOURI, Farnaz JAFARPOUR, Parviz RASHIDI RANJBAR, Abbas SHAFIEE, Mehdi KHOOBI

New Pd(II) and Pt(II)-diaminophosphine complexes bearing cyclohexyl or isopropyl moiety: use of Pd(II) complexes as precatalyst in Mizoroki--Heck and Suzuki--Miyaura cross-coupling reactions

Murat AYDEMİR, Feyyaz DURAP, Akin BAYSAL

Sonogashira reactions for the synthesis of polarized pentacene derivatives

Stephane SCHWEIZER, Guillaume ERBLAND, Philippe BISSERET, Jacques LALEVEE, Didier Le NOUEN, Nicolas BLANCHARD

A simple approach to bis-spirocycles and spiroindole derivatives via greenmethods such as Fischer indolization, ring-closing metathesis, andSuzuki{Miyaura cross-coupling

Rashid ALI, Sambasivarao KOTHA

Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki{Miyaura cross-couplings catalysts

Muhittin AYGÜN, Ümit İŞCİ, Yunus ZORLU, Fabienne DUMOULİN, Resul SEVİNCEK

Palladium-catalyzed ligand-free and efficient Suzuki--Miyaura reaction of $N$-methyliminodiacetic acid boronates in water

Chun LIU, Xinmin LI, Xinnan WANG, Jieshan QIU

Efficient C--C cross-coupling reactions by (isatin)-Schiff base functionalized magnetic nanoparticle-supported Cu(II) acetate as a magnetically recoverable catalyst

Seyedeh Simin MIRI, Mehdi KHOOBI, Fatemeh ASHOURI, Farnaz JAFARPOUR, Parviz Rashidi RANJBAR, Abbas SHAFIEE