α,α-Dioxoketene dithioacetals as starting materials for the synthesis of polysubstituted pyridines
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1449-1452
- https://doi.org/10.1039/p19940001449
Abstract
Reactions of 3-acetyl-4,4-bis(methylthio)but-3-en-2-one 2e and methyl 2-acetyl-3,3-bis(methylthio)prop-2-enoate 2f with cyanothioacetamide, cyanoacetamide, or 2-amino-1,3,3-tricyanoprop-1-ene and base, followed by treatment with acid, give polysubstituted pyridines such as 8,10,11,13,15 and 16. Further elaboration of these products leads to bicyclic systems such as thieno[2,3-b]pyridines 17 and 18 and pyrazolo[3,4-c]pyridine 21 and then to tricyclic systems including pyrazolo[3,4-d]thieno[2,3-b]pyridine 19 and dipyrazolo[3,4-b:3′4′-d] pyridine 22.Keywords
This publication has 11 references indexed in Scilit:
- Reaction of Ketene Dithioacetals with Thioamides. A Synthesis of Pyrimidine DerivativesHETEROCYCLES, 1992
- One-pot stereoselective synthesis and structural study of 1-methylthio-2-azabuta-1,3-diene-4-carbonitrilesJournal of the Chemical Society, Perkin Transactions 1, 1992
- Synthesis, Reactions, and Tautomerism of Ketene N,S‐Acetals with Benzothiazoline RingEuropean Journal of Inorganic Chemistry, 1990
- Ketene Dithioacetals in Organic Synthesis: Recent DevelopmentsSynthesis, 1990
- Synthesis of pyrimidine derivatives by the reaction of ketene dithioacetals with amidesJournal of Heterocyclic Chemistry, 1988
- Haller-Bauer cleavage of open-chain and cyclic .alpha.-phenyl ketones proceeds with retention of configurationJournal of the American Chemical Society, 1987
- α-Oxo ketene dithioacetals and related compounds: versatile three-carbon synthonsTetrahedron, 1986
- Dimerisation of 3-aryl-2-cyanothioacrylamides. A [2s+ 4s] cyclo-addition to give substituted 3,4-dihydro-2H-thiopyransJournal of the Chemical Society, Perkin Transactions 1, 1978
- Keten SS-acetals. Part 9. Reaction of α-oxo- and α-cyano-keten SS-acetals with cyanoacetamide: a new general method for substituted and fused 4-alkylthio-3-cyano-2(1H)-pyridones and formation of novel pyridones through base-induced rearrangementsJournal of the Chemical Society, Perkin Transactions 1, 1978
- Studies of Polarized Ethylenes. Part I. Barriers to Rotation Around the Carbon-Carbon Double Bond in 1,1-Bis-alkylthio-ethylenes.Acta Chemica Scandinavica, 1970