TAILIEUCHUNG - Verma et al. Organic and Medicinal Chemistry Letters 2011, 1:6

Verma et al. Organic and Medicinal Chemistry Letters 2011, 1:6 ORIGINAL Open Access [3 + 2] Cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid: a versatile route to new heterocyclic scaffolds Sonali Verma, Johnson George, Saurabh Singh, Pushpa Pardasani and Ramchand Pardasani* Abstract A facile synthesis of azabicycloadducts is described by 1,3-dipolar cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid in the presence of various electron rich and electron deficient dipolarophiles. Theoritical calculations have been performed to study the regioselectivity of products. The geometrical and energetic properties have been analyzed for the different reactants, transition states and cycloadducts formed. Keywords: Azabicycloadducts, 1,3-Dipolar cycloaddition reactions, AM1 Calculations, Thioisatin,. | Verma et al. Organic and Medicinal Chemistry Letters 2011 1 6 http content 1 1 6 o Organic and Medicinal Chemistry Letters a SpringerOpen Journal ORIGINAL Open Access 3 2 Cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid a versatile route to new heterocyclic scaffolds Sonali Verma Johnson George Saurabh Singh Pushpa Pardasani and Ramchand Pardasani Abstract A facile synthesis of azabicycloadducts is described by 1 3-dipolar cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid in the presence of various electron rich and electron deficient dipolarophiles. Theoritical calculations have been performed to study the regioselectivity of products. The geometrical and energetic properties have been analyzed for the different reactants transition states and cycloadducts formed. Keywords Azabicycloadducts 1 3-Dipolar cycloaddition reactions AM1 Calculations Thioisatin Thiazolidine-2-car-boxylic Acid Background The construction of sophisticated molecules requires viable selective and highly reliable reactions as potent synthetic tools 1-3 . The 1 3-dipolar cycloaddition 4-9 has also become one of the most important legation method in biology and material chemistry. Thioisatin derivatives 10 have received the attention of biochemists because of their therapeutic and biological activities. Similarly thiazolidine-2-carboxylic acid 11 12 exhibit strong antioxidant properties. Therefore any heterocyclic scaffold containing these two moieties might be expected to have considerably enhanced biological activities. The 1 3-dipolar cycloaddition reaction of an azo-methine ylide with an alkene leads to the formation of pyrrolidine 13 14 derivatives. Recently we have reported the results on azomethine ylides derived from 9 10-phenanthrenequinone and some secondary cyclic a-amino acids with different dipolarophiles 15 . Herein we report the reactivity and regioselectivity of 1 3-dipo-lar cycloaddition reactions of .

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