Short Guide

to Heterocycles

© GalChimia, S.L., 2005

Acridine Cinnoline
Adenine Coumaran
Azepine Coumarin
Azole Cyclopenta[b]pyridine
2H-Azole
3H-Azole
7-Deazapurine
7-Deaza-8-azapurine
Benzimidazole 9-Deazapurine
Benzisoxazole 4H-1,2-Diazepine
2,1-Benzisoxazole 1,2-Diazole
Benzofuran 1,3-Diazole
2H-1-Benzopyran 1,4-Dioxane
2H-1-Benzopyran-2-one 3H-1,2,3-Dioxazole
4H-1-Benzopyran-4-one 1,2,4-Dioxazole
1H-2-Benzopyran-1-one 1,3,2-Dioxazole
3H-2-Benzopyran-3-one 2H-1,3,4-Dioxazole
Benzothiazole 1,2-Dioxin
Benzo[b]thiophene 1,3-Dioxin
Benzo[c]thiophene 1,3-Dioxolane
1H-2,3-Benzoxazine 1,3-Dithiane
2H-1,3-Benzoxazine 1,4-Dithiane
2H-1,4-Benzoxazine 2H-1,3-Dithiole
4H-1,4-Benzoxazine 3H-1,2-Dithiole
4H-3,1-Benzoxazine
2H-1,2,4-Benzoxadiazine
Benzoxazole Furan
Furazan

Carbazole
Carbolines Guanine
α-Carboline
β-Carboline
γ-Carboline Hipoxanthine

δ-Carboline
2H-Chromene
Chromen-4-one Imidazolidine

Short Guide to Heterocycles - 1

1H-Imidazole 1,2,3,5-Oxatriazole
2H-Imidazole 5-Oxazolone
2-Imidazoline 5H-1,2,5-Oxathiazole
Imidazoline-2-thione 1,3-Oxathiole
Imidazo[1,5-a]pyrimidine 2H-1,2-Oxazine
1H-Indazole 2H-1,3-Oxazine
Indole 2H-1,4-Oxazine
3H-Indole 4H-1,2-Oxazine
Indoline 4H-1,4-Oxazine
Indoxazine 6H-1,2-Oxazine
Isobenzofuran 6H-1,3-Oxazine
Isochromen-3-one 1,2,5-Oxathiazine
Isocoumarin 1,2,6-Oxathiazine
1H-Isoindole 1,2,4-Oxadiazine
Isoquinoline 1,3,5-Oxadiazine
Isothiazole Oxepin
Isoxazole

Phenazine
Morpholine Phenothiazine
Phthalazine
Piperazine
1,5-Naphthyridine Piperidine
1,6-Naphthyridine Pteridine
1,7-Naphthyridine Purine
1,8-Naphthyridine 2H-Pyran
2H-Pyran-2-one
4H-Pyran-4-one
3H-1,2-Oxathiole Pyrano[3,4-b]pyrrole
Oxazole Pyrazine
1,2-Oxazole Pyrazole
1,3-Oxazole Pyrazolidine
1,2,3-Oxadiazole 2-Pyrazoline
1,2,4-Oxadiazole Pyrazolo[1,5-a]pyrimidine
1,2,5-Oxadiazole 1H-Pyrazolo[3,4-d]pyrimidine
1,3,4-Oxadiazole Pyridazine
1,2,3,4-Oxatriazole Pyridine

Short Guide to Heterocycles - 2

Pyrimidine 1,3,5-Trithiane
2-Pyrone Thiepin
4-Pyrone Thymine
Pyrrole
2H-Pyrrole
3H-Pyrrole Uracil
Pyrrolidine
2-Pyrroline
3-Pyrroline Xanthene
5H-pyrrolo[3,2-d]pyrimidine Xanthine
7H-pyrrolo[2,3-d]pyrimidine

Quinazoline
Quinoline
4H-Quinolizine
Quinoxaline
Quinuclidine

Tetrahydrofuran
Tetrahydrothiophene
Thiophene
1,2,3-Triazole
1,2,4-Triazole
2-Thiazoline
Thiazole
1,3-Thiazole
1,2-Thiazole
1,3,4-Thiadiazole
1,3,5-Triazine
s-Triazine
1,2,4-Triazine
as-Triazine
1,2,3-Triazine
v-Triazine
Thiomorpholine

Short Guide to Heterocycles - 3

 4 3 4 3 4 3

5 2 5 2 5 2
1N 1N 1N
H H H
Pyrrolidine 3-Pyrroline 2-Pyrroline
4 3 4 5 5 1
N
5 2 3 N1 4 2
1N 2
H 3

Pyrrole 2H-Pyrrole 3H-Pyrrole

(Azole) (2-Azole) (3-Azole)

4 3 4 3

5 2 5 2
O O
1 1

Furan Tetrahydrofuran

4 3 4 3

5 2 5 2
S S
1 1

Thiophene Tetrahydrothiophene

4 3 4 3 4 3

5 NH 5 N2 5 N2
2
1N 1N 1N
H H H
Pyrazolidine 2-Pyrazoline Pyrazole
(1,2-Diazole)

4 H3 4 3
N N
2 5 2
5
1N 1N
H H
Imidazolidine 2-Imidazolidine

Short Guide to Heterocycles - 5

 4 3 4 3
N N
5 2 5 2
1N N
H 1

1H-Imidazole 2H-Imidazole
(1,3-Diazole)

4 3 4 3
N N
5 N2 5 N2
1N 1N
H H
1,2,3-Triazole 1,2,4-Triazole

4 3
O
5 2
O
1

1,3-Dioxolane

4 3 4 3 4 3
S S
5 S2 5 2 5 2
S S S
1 1 1

3H-1,2-Dithiole 1,3-Dithiolane 2H-1,3-Dithiole

4 3 4 3
N
5 N2 5 2
O O
1 1

Isoxazole Oxazole
(1,2-Oxazole) (1,3-Oxazole)

4 3
N
5 2
S
1

2-Thiazoline

Short Guide to Heterocycles - 6

 4 3 4 3
N
5 N2 5 2
S S
1 1

Isothiazole Thiazole
(1,2-Thiazole) (1,3-Thiazole)

4 3 4 3
S
5 S2 5 2
O O
1
1

3H-1,2-Oxathiole 1,3-Oxathiole

4 3 4 3 4 3
N N
5 N2 5 N2 5N N2
O O O
1 1 1

1,2,3-Oxadiazole 1,2,4-Oxadiazole 1,2,5-Oxadiazole

(Furazan)
4 3
N N
5 2
O
1

1,3,4-Oxadiazole

4 3 4 3
N N N
5 N2 5N N2
O O
1 1

1,2,3,4-Oxatriazole 1,2,3,5-Oxatriazole

4 H3 4 3 4 3
N N O
5 O2 5 O2 5 NH
O O 2
O 1 1
1

3H-1,2,3-Dioxazole 1,2,4-Dioxazole 1,3,2-Dioxazole

Short Guide to Heterocycles - 7

 4 3
N O
5 2
O
1

2H-1,3,4-Dioxazole

4 3
N
5
2
O O
1

5-Oxazolone

4 3

HN S2
5 O
1

5H-1,2,5-Oxathiazole

4 H3
N
2
5
S
1N
H
Imidazoline-2-thione

4 3
N N
5 2
S
1

1,3,4-Thiadiazole

Short Guide to Heterocycles - 8

 4
5 3

6 2
O
1

2H-Pyran

4 O
5 3
4
5 3
6 2
O O
1 6 2
O
1

2H-Pyran-2-one 4H-Pyran-4-one
(2-Pyrone) (4-Pyrone)

4 4 4
5 3 5 O
3
5
O 3

6 O2 6 2 6 2
O O O
1 1 1

1,2-Dioxine 4H-1,3-Dioxine 1,4-Dioxane

4 4
5 3 5 3

6 2 6 2
N1 N
H 1

Piperidine Pyridine

4H
5
N 3

6 2
N1
H
Piperazine

Short Guide to Heterocycles - 9

 4 4 4
5 3 5 N
3
5
N 3

6 N2 6 2 6 2
N N N
1 1
1

Pyridazine Pyrimidine Pyrazine

4 4 4
5 3 N 5
N N
3
N 5 3

6 N2 6 N2 6 2
N N N
1 1
1

1,2,3-Triazine 1,2,4-Triazine 1,3,5-Triazine

(v-Triazine) (as-Triazine) (s-Triazine)

4 4 4
5 3 5 3 N
N 5 3

6 NH 6 2 6 2
O 2 O O
1 1 1

2H-1,2- Oxazine 2H-1,3- Oxazine 2H-1,4- Oxazine

4 H 4
5 3
5
N 3
5 3
4
6 N2 6 N2
O 6 2 O
1 O 1
1

4H-1,2-Oxazine 4H-1,4-Oxazine 6H-1,2-Oxazine

4
5 3
N
6 2
O
1

6H-1,3-Oxazine

H
5
N 3
4

6 2
O
1

Morpholine

Short Guide to Heterocycles - 10

 H
5
N 3
4

6 2
S
1

Thiomorpholine

H 4

5
N 3
5
N N
3
4

6 2
6 N2 O
O 1
1

1,2,4-Oxadiazine 1,3,5-Oxadiazine

4 4
5 3 5 3
N
6 S2 6N S2
O O
1 1

1,2,5-Oxathiazine 1,2,6-Oxathiazine

4 4
5 S 3
5
S 3

6 2 6 2
S S
1
1

1,3-Dithiane 1,4-Dithiane

4
5
S S3
6 2
S
1

1,3,5-Trithiane

Short Guide to Heterocycles - 11

 5 4 5 4

6 3 6 3

7 2 7 N2
N1 N
H 1

Azepine 4H-1,2-Diazepine

5 4

6 3

7 2
O
1

Oxepin

5 4

6 3

7 2
S
1

Thiepin

4
5 3
7 8
6 2
N
1

Quinuclidine

Short Guide to Heterocycles - 12

 4 3 4 3 4 3
5 5 5
2 2 2
6 6 6
N1 N1 N
7 H 7 H 7 1

Indoline 1H-Indole 3H-Indole

4 3
5
N2
6
7 1

1H-Isoindole

4 3 4 3 4 3
5 5 5
2 2 O2
6 6 6
O O 1
7 1 7 1 7

Coumaran Benzofuran Benzo[c]furan

4 3 4 3
5 5
2 S2
6 6
S 1
7 1 7

Benzo[b]thiophene Benzo[c]thiophene

4 3 4 3
4 H3
5 5 N 5 N
N2 2 O
2
6 6
N1 N1 6
N1
7 H 7 H 7 H
1H-Indazole Benzimidazole 1,3-dihydro-2H-
benzimidazol-2-one

4 5
3
6
2
N 7
1

Cyclopenta[b]pyridine

Short Guide to Heterocycles - 13

 4 3 4 3 4 3
5 5 N 5
N2 2 O2
6 6 6
O O N
7 1 7 1 7 1

Benzisoxazole Benzoxazole 2,1-Benzisoxazole

(Indoxazine)

4 3
5
2
6O N
7 1

Pyrano[3,4-b]pyrrole

4 3
5 N
2
6
S
7 1

Benzothiazole

Short Guide to Heterocycles - 14

 5 4 5 4 6 4
5
6 3 6 3 7 3
N
7 2 7 N2 8 2
8 N 8 1 9 1
1

Quinoline Isoquinoline 4H-Quinolizine

5 4 5 4 O
6 3 6 3 5 4
6 3
7 2 7 2
8 O 8 O O
1 1 7 2
8 O
1

2H-1-Benzopyran 2H-1-Benzopyran-2-one 4H-1-Benzopyran-4-one

(2-Chromene) (Coumarin) (Chromen-4-one)

5 4 5 4
3 3 O
6 6

7 O2 7 O2
8 1 8 1
O
1H-2-Benzopyran-1-one 3H-2-Benzopyran-3-one
(Isocoumarin) (Isochromen-3-one)

5 4 5 4 4
5
6 3 6 N
3 N 3
6

7 N2 7 2 7 2
8 N 8 N N
1 1 8 1

Cinnoline Quinazoline Quinoxaline

5 4
6 3
N
7 N2
8 1

Phthalazine

Short Guide to Heterocycles - 15

 5 4 5 4 5 4
N 6 3 6 3
6 3 N

7 2 7 2 7N 2
N 8 N 8 N
8 1 1 1

1,5-Naphthyridine 1,6-Naphthyridine 1,7-Naphthyridine

5 4
6 3

7 2
N N
8 1

1,8-Naphthyridine

5 4
5
4
5 H
6 N
3 N 3 N
6 6 4 3

7 2 7 2
O O
7 2
8 1 8 1 8 O
1

2H-1,3-Benzoxazine 2H-1,4-Benzoxazine 4H-1,4-Benzoxazine

5 4 5 4
6 3 6 3
N O
7 O2 7 2
8 1 8 N
1

1H-2,3-Benzoxazine 4H-3,1-Benzoxazine

4
5
N 3
6

7 NH
8 O 2
1

2H-1,2,4-benzoxadiazine

5 4
6
N 3
N
7 2
N N
8 1

Pteridine

Short Guide to Heterocycles - 16

 6 5 4 3

7 2

8 N9 1
H
Carbazole

6 5 4 6 5 4 6 5 4 3
3 3
N
7 2 7 N2 7 2
N
8 N9 1 8 N9 1 8 N9 1
H H H
α-Carboline β-Carboline γ-Carboline
5 4
6 N 3

7 2

8 N9 1
H
δ-Carboline

Short Guide to Heterocycles - 17

 8 9 1
7 2

6 3
5 N 4
10

Acridine

8 9 1
7 2

6 3
5 O 4
10

Xanthene

9 1
8
N 2
7

6 3
5 N 4
10

Phenazine

5 4
6
O 3
7

8 2
9 N 10 1
H
Phenoxazine

5 4
6
S 3
7

8 2
9 N 10 1
H
Phenothiazine

Short Guide to Heterocycles - 18

 6 7 NH2 O
1
N
5 N 7 7
6 1 6
8 1 5 N 5 N
2
N HN
N
4 N9 8 8
3 H 2
N
4 N9 H2N
2
N
4 N9
3 H 3 H
Purine Adenine Guanine

O O
6 9 6 9
1 1
5 N 5 N
HN HN
8 8
2
O
2
N3
4 N7 N
4 N7
H H 3 H
Xanthine Hipoxanthine

O O NH2
3 4 3 4 4
5 3
HN HN 5 N 5
2 2 2
6 6 6
O 1N O 1N O 1N
H H H
Uracil Thymine Cytosine

5
4 3 4 H5
N 3 N
2 N
6
6
N N1 2
7 H N 7
1

7H-Pyrrolo[2,3-d]pyrimidine 5H-Pyrrolo[3,2-d]pyrimidine
(7-Deazapurine) (9-Deazapurine)

4 1
5 N 3 N 8
2
2 N7
6 N 3 N
8 N 5 6
7 1 4

Pyrazolo[1,5-a]pyrimidine Imidazo[1,5-a]pyrimidine

Short Guide to Heterocycles - 19

 4 3
5
N
N2
6
N N1
7 H
1H-Pyrazolo[3,4-d]pyrimidine
(7-Deaza-8-azapurine)

Short Guide to Heterocycles - 20