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Your search keyword '"3-Nitrothiophene"' showing total 2 results
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2 results on '"3-Nitrothiophene"'

1. A new route to thiopyran S,S-dioxide derivatives via an overall ring-enlargement protocol from 3-nitrothiophene

Author

Bianchi, Lara, Maccagno, Massimo, Petrillo, Giovanni, Rizzato, Egon, Sancassan, Fernando, Severi, Elda, Spinelli, Domenico, Stenta, Marco, Galatini, Andrea, and Tavani, Cinzia

Subjects
*PYRAN, *THIOPHENES, *BUTADIENE, *RING formation (Chemistry), *SULFUR compounds, *OXIDES, *HETEROCYCLIC compounds
Abstract

Abstract: (1E,3Z)-1-Aryl-4-methanesulfonyl-2-nitro-1,3-butadienes (8), derived from the initial ring-opening of 3-nitrothiophene (5), have been found to undergo a facile base-induced cyclization leading to thiopyran S,S-dioxides (9), thus furnishing a further example of effective ring-enlargement from 5- to 6-membered sulfur heterocycles. Compounds 9 are obtained as single racemic mixtures in satisfactory yields; they still contain a nitrovinylic moiety, which can be exploited for further modifications targeted to new derivatives endowed with either synthetic or pharmacological potentialities e.g., in the field of L-type Ca2+-channel blockers. [Copyright &y& Elsevier]

Published
2009
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2. A new route to thiopyran S,S-dioxide derivatives via an overall ring-enlargement protocol from 3-nitrothiophene

Author

Elda Severi, Domenico Spinelli, Massimo Maccagno, Cinzia Tavani, Andrea Galatini, Lara Bianchi, Egon Rizzato, Marco Stenta, Fernando Sancassan, and Giovanni Petrillo

Subjects
chemistry.chemical_classification, Thiopyran, Ring-opening/ring-closing reactions, Stereochemistry, Ring-enlargement protocol, Organic Chemistry, Nitro compound, chemistry.chemical_element, Ring expansion, Ion calcium, Ring (chemistry), Biochemistry, Combinatorial chemistry, Sulfur, Chemical synthesis, Sulfone, 3-Nitrothiophene, chemistry.chemical_compound, chemistry, Thiopyran S, S-dioxides, Drug Discovery, Moiety, 3-Nitrothiophene, Ring-opening/ring-closing reactions, Ring-enlargement protocol, Sulfur heterocycles, Ring expansion, Thiopyran S,S-dioxides, Sulfur heterocycles
Abstract

(1 E ,3 Z )-1-Aryl-4-methanesulfonyl-2-nitro-1,3-butadienes ( 8 ), derived from the initial ring-opening of 3-nitrothiophene ( 5 ), have been found to undergo a facile base-induced cyclization leading to thiopyran S , S -dioxides ( 9 ), thus furnishing a further example of effective ring-enlargement from 5- to 6-membered sulfur heterocycles. Compounds 9 are obtained as single racemic mixtures in satisfactory yields; they still contain a nitrovinylic moiety, which can be exploited for further modifications targeted to new derivatives endowed with either synthetic or pharmacological potentialities e.g., in the field of L-type Ca 2+ -channel blockers.

Published
2009
Full Text
View/download PDF

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