Tributylphosphine promoted domino reaction for efficient construction of spiro[cyclohexane-1,3'-indoline] and spiro[indoline-3,2'-furan-3',3''-indoline]

Submitting author affiliation:
Yangzhou University, Yangzhou, China

Beilstein Arch. 2022, 202226. https://doi.org/10.3762/bxiv.2022.26.v1

Published 21 Apr 2022

Preprint

Abstract

Tributylphosphine catalyzed reaction of isatylidene malononitriles and bis-chalcones in chloroform at 65oC afforded the functionalized spiro[cyclohexane-1,3'-indolines] in good yields and with good diastereoselectivity. On the other hand, tributylphosphine catalyzed reaction of 3-(ethoxycarbonylmethylene)oxindoles and bis-chalcones gave functionalized spiro[cyclohexane-1,3'-indolines] with different regioselectivity. Additionally, tributylphosphine domino promoted annulation reaction of isatins and ethyl isatylidene cyanoacetates produced spiro[indoline-3,2'-furan-3',3''-indolines] in satisfactory yields.

Keywords: tributylphosphine; spiroxindole; isatin; spiro[cyclohexane-1,3'-indoline]; spiro[indoline-3,2'-furan-3',3''-indoline].

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Zheng, H.; Han, Y.; Sun, J.; Yan, C.-G. Beilstein Arch. 2022, 202226. doi:10.3762/bxiv.2022.26.v1

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