An Efficient Synthesis of α‐Isothiocyanato‐α,β‐unsaturated Esters from Morita–Baylis–Hillman Adducts

Kim, Ko Hoon; Kim, Su Yeon; Lee, Ji Min; Kim, Jae Nyoung

doi:10.1002/bkcs.10705

Cited by 6 publications

(4 citation statements)

References 35 publications

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“…18). 90,91 These esters possess diverse reactivities that are useful for the synthesis of various heterocyclic compounds. They utilized a,bunsaturated ester 13-1 as the precursor of a-isothiocyanatoa,b-unsaturated esters.…”

Section: Recent Advances In Isothiocyanate Synthesis With Type Bmentioning

confidence: 99%

Recent advancement in the synthesis of isothiocyanates

Maeda,

Murakami

2024

Chem. Commun.

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Section: Recent Advances In Isothiocyanate Synthesis With Type Bmentioning

confidence: 99%

Recent advancement in the synthesis of isothiocyanates

Maeda,

Murakami

2024

Chem. Commun.

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“…[89] The reaction of the cyclic amidine with CS2 afforded cyclic carbamic carboxylic trithioanhydride In 2016, Kim developed an efficient synthetic method for α-isothiocyanato-α,β-unsaturated esters (Figure 17). [90] These esters possess diverse reactivities that are useful for the synthesis of various heterocyclic compounds. Traditional approaches for synthesizing α-isothiocyanato-α,βunsaturated esters involved the Staudinger reaction with PPh3 to form iminophosphorane and aza-Wittig reaction with CS2.…”

Section: -3 22%mentioning

confidence: 99%

Recent Advancement in Synthesis of Isothiocyanates

Maeda,

Murakami

2023

Preprint

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Isothiocyanates exhibit various biological characteristics, including antimicrobial, anti-inflammatory, and anticancer properties. Their significance extends to synthetic chemistry, where they serve as valuable platforms for versatile transformations. Consequently, they have attracted the attention of biologists and chemists. This review summarizes recent advancements in the synthesis of isothiocyanates. Access to a variety of starting materials is important to prepare isothiocyanates with diverse structures. This review categorizes synthetic methods into three types based on the starting materials and functional groups: (i) Type A, derived from primary amines; (ii) Type B, derived from other nitrogen functional groups; and (iii) Type C, derived from non-nitrogen groups. Recent trends in synthetic methods have revealed the prevalence of type-A reactions derived from primary amines. However, Type B reactions have rarely been reported. Notably, over the past four years, there has been a notable increase in Type C reactions, indicating a growing interest in non-nitrogen-derived isothiocyanates. Overall, this review not only outlines the advancements in the synthesis of isothiocyanates but also highlights trends in the methodology.

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“…Several methods for the isothiocyanation of alkenyl compounds such as sulfur transfer to alkenyl isocyanide, 16 the combination of Staudinger reaction and aza-Wittig reaction with alkenyl azides, 17 and isothiocyanation via 1,3-dipolar cycloaddition and rearrangement 18 have been reported. Additionally, in 2016, the Kim group accomplished the synthesis of α-isothiocyanato-α,β-unsaturated esters from allyl nitro compounds, which are useful for the synthesis of heterocycles 19 (Scheme 2B). Recently, one synthetic approach of N -vinyl isothiocyanate from triazole utilizing thiophosgene was reported by Motornov and Beier.…”

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confidence: 99%