Composto eterociclico

Principali composti eterociclici

Un composto eterociclico è una molecola ciclica nella quale uno o più atomi dell'anello sono eteroatomi, cioè atomi diversi dal carbonio. Gli eteroatomi più comuni sono: l'azoto, l'ossigeno, lo zolfo, il fosforo, il boro, il silicio. Ciascuno di essi dà origine a vaste famiglie di composti eterociclici.

La piridina e la pirimidina sono eterocicli analoghi del benzene, mentre il pirrolo e l'imidazolo sono analoghi del ciclopentadiene. Il glucosio e il ribosio in forma ciclica sono composti eterociclici, in quanto all'interno dell'anello è presente un atomo di ossigeno.

Esistono inoltre una moltitudine di composti eterociclici ad anelli condensati, tra cui l'indolo e la purina, che rivestono anch'essi grande importanza in biologia.

Classificazione

Una prima classificazione dei composti eterociclici si basa sul carattere aromatico o meno dell'anello che include l'eteroatomo. Si possono così distinguere composti eterociclici non aromatici ed eterociclici aromatici.

Anelli eterociclici singoli

Anelli a 3 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Aziridina Azirina
Ossigeno Ossirano Ossirene
Zolfo Tiirano Tiirene
2 × Azoto Diaziridina Diazirina
2 × Ossigeno Diossirano Diossirene
2 × Zolfo Ditiirano Ditiirene

Anelli a 4 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Azetidina Azete
Ossigeno Ossetano Ossete
Zolfo Tietano Tiete
2 × Azoto Diazetidina Diazete
2 × Ossigeno Diossetano Diossete
2 × Zolfo Ditietano Ditiete

Anelli a 5 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Pirrolidina Pirrolo
Pirrolina
Ossigeno Ossolano Furano
Zolfo Tiolano Tiofene
Fosforo Fosfolano Fosfolo
Boro Borolano Borolo
Silicio Silolano Silolo
2 × Azoto Pirazolidina
Imidazolidina 		Pirazolo
Imidazolo
Pirazolina
Imidazolina
2 × Ossigeno Diossolano Diossolo
2 × Zolfo Ditiolano Ditiolo
Azoto + Ossigeno Ossazolidina
Isossazolidina 		Ossazolo
Isossazolo
Ossazolina
Isossazolina
Azoto + Zolfo Tiazolidina
Isotiazolidina 		Tiazolo
Isotiazolo
Tiazolina
Isotiazolina
Ossigeno + Zolfo Ossatiolano
Isossatiolano 		Ossatiolo
Isossatiolo

Anelli a 6 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Piperidina Piridina
Ossigeno Ossano Pirano
Zolfo Tiano Tiopirano
Fosforo Fosfinano Fosfinina
Boro Borinano Borinina
Silicio Silinano Silinina
2 × Azoto Piperazina
Piperimidina
Piperidazina 		Pirazina
Pirimidina
Piridazina
2 × Ossigeno Diossano Diossina
2 × Zolfo Ditiano Ditiina
Azoto + Ossigeno Morfolina Ossazina
Azoto + Zolfo Tiomorfolina Tiazina
Ossigeno + Zolfo Ossatiano Ossatiina

Anelli a 7 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Azepano Azepina
Ossigeno Ossepano Ossepina
Zolfo Tiepano Tiepina
2 × Azoto Diazepano Diazepina
2 × Ossigeno Diossepano Diossepina
2 × Zolfo Ditiepano Ditiepina

Anelli a 8 atomi

Eteroatomi Composti
saturi 		Composti
insaturi
Azoto Azocano Azocina
Ossigeno Ossocano Ossocina
Zolfo Tiocano Tiocina
2 × Azoto Diazocano Diazocina
2 × Ossigeno Diossocano Diossocina
2 × Zolfo Ditiocano Ditiocina

Anelli eterociclici doppi

Anelli a 5 atomi condensati con anelli a 6 atomi

Anelli singoli Anello doppio
Benzene + Pirrolo Indolo
Isoindolo
Benzene + Pirazolo Indazolo
Benzene + Imidazolo Benzimidazolo
Benzene + Furano Benzofurano
Isobenzofurano
Benzene + Tiofene Benzotiofene
Isobenzotiofene
Benzene + Ossazolo Benzossazolo
Benzene + Isossazolo Benzisossazolo
Benzene + Tiazolo Benzotiazolo
Benzene + Isotiazolo Benzisotiazolo
Piridina + Pirrolo Azaindolo
Piridina + Pirazolo Azaindazolo
Pirimidina + Imidazolo Purina

Anelli a 6 atomi condensati con anelli a 6 atomi

Anelli singoli Anello doppio
Benzene + Piridina Chinolina
Isochinolina
Benzene + Pirazina Chinossalina
Benzene + Pirimidina Chinazolina
Benzene + Pirano Cromene
Isocromene
Benzene + Tiopirano Tiocromene
Isotiocromene
Benzene + Ossazina Benzossazina
Benzene + Tiazina Benzotiazina
Piridina + Pirazina Piridopirazina
Piridina + Pirimidina Piridopirimidina
Pirazina + Pirimidina Pteridina

Anelli eterociclici tripli

Anelli singoli Anello triplo
2 × Benzene + Pirrolo Carbazolo
2 × Benzene + Furano Dibenzofurano
2 × Benzene + Tiofene Dibenzotiofene
2 × Benzene + Piridina Acridina
2 × Benzene + Pirano Xantene
2 × Benzene + Tiopirano Tioxantene
2 × Benzene + Pirazina Fenazina
2 × Benzene + Ossazina Fenossazina
2 × Benzene + Tiazina Fenotiazina

Struttura molecolare

Composti saturi Composti insaturi
Eteroatomo Azoto Ossigeno Zolfo Azoto Ossigeno Zolfo
Anelli a 3 atomi Aziridina Ossirano Tiirano Azirina Ossirene Tiirene
Structure of aziridine Structure of oxirane Structure of thiirane Structure of azirine Structure of oxirene Structure of thiirene
Anelli a 4 atomi Azetidina Ossetano Tietano Azete Ossete Tiete
Structure of azetidine Structure of oxetane Structure of thietane Structure of azete Structure of oxete Structure of thiete
Anelli a 5 atomi Pirrolidina Ossolano Tiolano Pirrolo Furano Tiofene
Structure of pyrrolidine Structure of oxolane Structure of thiolane Structure of pyrrole Structure of furan Structure of thiophene
Anelli a 6 atomi Piperidina Ossano Tiano Piridina Pirano Tiopirano
Structure of piperidine Structure of oxane Structure of thiane Structure of pyridine Structure of pyran Structure of thiopyran
Anelli a 7 atomi Azepano Ossepano Tiepano Azepina Ossepina Tiepina
Structure of azepane Structure of oxepane Structure of thiepane Structure of azepine Structure of oxepine Structure of thiepine
Anelli a 8 atomi Azocano Ossocano Tiocano Azocina Ossocina Tiocina
Structure of azocane Structure of oxocane Structure of thiocane Structure of azocine Structure of oxocine Structure of thiocine

Nomenclatura

Per i composti eterociclici, la nomenclatura IUPAC è notevolmente complessa, soprattutto per le molecole contenenti due o più anelli.

La prima tabella riporta i prefissi da utilizzare per i relativi eteroatomi principali in ordine di priorità:

Elemento Simbolo Prefisso
Ossigeno O ossa-
Zolfo S tia-
Selenio Se selena-
Tellurio Te tellura-
Azoto N aza-
Fosforo P fosfa-
Arsenico As arsa-
Antimonio Sb stiba-
Bismuto Bi bisma-
Silicio Si sila-
Germanio Ge germa-
Boro B bora-

La a finale dei prefissi in genere si perde se seguita da altra vocale o si assimila ad essa.

La seconda tabella riporta i suffissi per indicare il numero di atomi dell'anello. Si distinguono gli anelli che contengono azoto da quelli che non lo contengono:

Numero atomi Azotati insaturi Azotati saturi Non azotati insaturi Non azotati saturi
3 -irina -iridina -irene -irano
4 -ete -etidina -ete -etano
5 -olo -olidina -olo -olano
6 -ina -inano[1] -(in)ina -(in)ano
7 -epina -epano[1] -epina -epano
8 -ocina -ocano[1] -ocina -ocano
9 -onina -onano[1] -onina -onano
10 -ecina -ecano[1] -ecina -ecano

La molteplicità dello stesso eteroatomo si realizza con i prefissi di-, tri-, tetra-...

Per eteroatomi diversi si uniscono i prefissi nell'ordine ossigeno, zolfo, azoto.

Gli atomi di carbonio uniti ad altri due con legami semplici vengono indicati con il prefisso H- al nome del composto preceduto da un numero indicante la posizione.

Anelli ciclici aventi un nome consacrato dall'uso possono essere considerati la base su cui innestare successivi cicli come nella terza tabella:

Nome tradizionale Nome IUPAC Prefisso
antracene antracene antra-
benzene benzene benzo-
diossina 1,4-diossina diossino-
furano ossolo furo-
imidazolina 1,4,5H-1,3-diazolo imidazolino-
imidazolo 1H-1,3-diazolo imidazolo-
isossazolo 1,2-ossazolo isossazolo-
naftalene naftalene nafta-
ossazina 1,4-ossazina ossazino-
ossazolo 1,3-ossazolo ossazolo-
pirano ossina pirano-
pirazina 1,4-diazina pirazino-
pirazolina 1,4,5H-1,2-diazolo pirazolino-
pirazolo 1H-1,2-diazolo pirazolo-
pirene pirene piro-
piridina azina pirido-
pirrolina 1,4,5H-azolo pirrolino-
pirrolo 1H-azolo pirrolo-

Presenza in natura

L'importanza dei composti eterociclici, soprattutto quelli azotati, risiede nel loro ruolo, quasi sempre indispensabile, nei sistemi biologici. Molte vitamine, farmaci, droghe e altre sostanze naturali contengono anelli di composti eterociclici.

Note

  1. ^ a b c d e In alternativa si può aggiungere il prefisso peridro- al nome del composto insaturo corrispondente.

Bibliografia

Voci correlate

Altri progetti

Collegamenti esterni

Controllo di autoritàThesaurus BNCF 23305 · LCCN (EN) sh85060525 · BNE (ES) XX528450 (data) · BNF (FR) cb12117283k (data) · J9U (EN, HE) 987007557898905171 · NDL (EN, JA) 00563641
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