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Intramolecular Cycloaddition Approach to Fused Pyrazoles: Access to 4,5-Dihydro-2H-pyrazolo[4,3-c]quinolines, 2,8-Dihydroindeno[2,1-c]pyrazoles, and 4,5-Dihydro-2H-benzo[e]indazoles
Synthesis ( IF 2.6 ) Pub Date : 2017-12-12 , DOI: 10.1055/s-0036-1591737
Chinmay Chowdhury , Moumita Jash , Bimolendu Das , Suparna Sen

Abstract

A straightforward and efficient method for the synthesis of pyrazoles fused with 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1H-indene­, or 1,2,3,4-tetrahydronaphthalene involves the formation of the tosylhydrazone from an aromatic substrate carrying aldehyde and acetylenic functionalities at appropriate positions, followed by base-promoted generation of the diazo compound and subsequent intramolecular 1,3-dipolar cycloaddition. A number of functional groups were found to be compatible for this reaction sequence and yields were moderate to very good (44–95%). A plausible reaction mechanism supported by DFT calculations has been provided to explain the formation of products.

A straightforward and efficient method for the synthesis of pyrazoles fused with 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1H-indene­, or 1,2,3,4-tetrahydronaphthalene involves the formation of the tosylhydrazone from an aromatic substrate carrying aldehyde and acetylenic functionalities at appropriate positions, followed by base-promoted generation of the diazo compound and subsequent intramolecular 1,3-dipolar cycloaddition. A number of functional groups were found to be compatible for this reaction sequence and yields were moderate to very good (44–95%). A plausible reaction mechanism supported by DFT calculations has been provided to explain the formation of products.



中文翻译:

熔融吡唑的分子内环加成法:获得4,5-二氢-2H-吡唑并[4,3-c]喹啉,2,8-二氢茚并[2,1-c]吡唑和4,5-二氢-2H-苯并[e]吲唑

摘要

一种直接有效的合成与1,2,3,4-四氢喹啉,2,3-二氢-1 H-茚或1,2,3,4-四氢萘稠合的吡唑的方法涉及从以下位置形成甲苯磺酰hydr在适当的位置带有醛和炔官能团的芳族底物,然后碱促进重氮化合物的生成以及随后的分子内1,3-偶极环加成。已发现许多官能团可与该反应顺序相容,并且产率中等至非常好(44–95%)。已经提供了由DFT计算支持的合理的反应机理来解释产物的形成。

一种直接有效的合成与1,2,3,4-四氢喹啉,2,3-二氢-1 H-茚或1,2,3,4-四氢萘稠合的吡唑的方法涉及从以下位置形成甲苯磺酰hydr在适当的位置带有醛和炔官能团的芳族底物,然后碱促进重氮化合物的生成以及随后的分子内1,3-偶极环加成。已发现许多官能团可与该反应顺序相容,并且产率中等至非常好(44–95%)。已经提供了由DFT计算支持的合理的反应机理来解释产物的形成。

更新日期:2017-12-12
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